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Chemical Structure| 15687-27-1
Chemical Structure| 15687-27-1

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CAS No.: 15687-27-1

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Ibuprofen is an anti-inflammatory inhibitor targeting COX-1 and COX-2 with IC50 of 13 μM and 370 μM, respectively, and is used for pain relief, fever reduction and for reducing swelling.

Synonyms: DL-Ibuprofen;NSC 256857;Ibuprofen, Advil, Motrin, Nurofen, Brufen;U-18753;(±)-Ibuprofen

4.5 *For research use only!

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Semenya, Julius ; Yang, Yuanjie ; Lee, Hye Joon , et al.

Abstract: Carbon-heteroatom bonds are of great importance due to their prevalence in pharmaceuticals, agrochemicals, materials, and natural products. Despite the effective use of metal-catalyzed crosscoupling reactions between sp2-hybridized organohalides and soft heteroatomic nucleophiles for carbon-heteroatom bond formation, the use of sp3-hybridized organohalides remain limited and the coupling with thiols remains elusive. Here, we report the coupling of sp3-hybridized benzyl or tertiary halides with soft thiol nucleophiles catalyzed by iron and extend the utility to alcohol and amine nucleophiles. The reaction is broad in substrate scope for both coupling partners and applicable in the construction of congested tri- and tetrasubstituted carbon centers as well as β-quaternary heteroatomic products. The synthetic utility is further emphasized by gram-scale synthesis and rapid herbicide library synthesis. Overall, we provide an efficient method to prepare pharmaceutically and materially relevant carbon-heteroatom bonds by expanding iron-catalyzed cross-coupling reactions to the coupling of sp3-hybridized organohalides with soft nucleophiles.

Edyta Kucharska ; Berin Ok ; Anna Nowak , et al.

Abstract: This study assesses ibuprofen’s permeability to different formulations and their biodegradation. Hydrogel, organogel, Eucerin ointment, silicone ointment, and zinc ointment were investigated. The objective was to comprehensively evaluate the therapeutic efficacy and environmental implications of these formulations. Diverse formulations were examined through the utilisation of Franz diffusion chambers to evaluate the in vitro permeability of both ibuprofen and ibuprofenate sodium. Moreover, biodegradation studies of the obtained formulations were carried out with activated sludge. The activity of the inoculum was confirmed by using SDS as a reference compound. The experimental settings used (carbon content and inoculum volume) were selected based on the criteria set by the OECD guidelines. Relevant parameters pertaining to the biodegradation process were estimated, including biodegradation values (%B) at specific time points, half-lives of initial compounds and API-containing formulations, and degradation phases (lag phase I; degradation phase II, and plate phase III). For comparison purposes, biodegradation studies were also carried out for the initial IBU and IBUNa compounds under the same conditions. The environmental implications of these findings underscore the need for a balanced consideration of therapeutic efficacy and environmental sustainability in pharmaceutical formulation design. This study provides valuable insights for pharmaceutical researchers, environmental scientists, and regulatory bodies involved in the development and assessment of drug formulations. The proposed method of removing NSAIDs from aquatic ecosystems is a cheaper alternative to techniques such as reverse osmosis, oxidation, UV degradation, or photolysis, which have not found practical use owing to the generation of toxic sludge or high capital and operating costs.

Keywords: permeability ; biodegradability ; ibuprofen ; nonsteroidal anti-inflammatory drug ; drug formulation

Purchased from AmBeed: ;

Klebeko, Joanna ; Ossowicz-Rupniewska, Paula ; Nowak, Anna , et al.

Abstract: Herein, we investigated the effect of pairing the L-amino acid alkyl (Pr, iso-Pr, or butyl) ester on the formation of API-ILs. The novel salts of NSAIDs (non-steroidal anti-inflammatory drugs) obtained from biodegradable cations were synthesized and characterised by NMR (NMR), Fourier transform IR spectroscopy (FT-IR), and X-ray powder diffraction (XRD) methods. The influence of structure counterions for APIs from the NSAIDs group on their physicochem. properties was studied in detail. The comprehensive effects of cation structure on skin permeation, accumulation, and antioxidant activity of API-ILs were also evaluated. These results demonstrated that L-amino acid alkyl esters can be successfully used to synthesize API-ILs further used in topical formulations with anti-ageing, anti-inflammatory, or photoprotective effects.

Keywords: Nonsteroidal anti-inflammatory drug ; Amino acid ester salts ; Ionic liquids ; Topical delivery ; Skin barrier

Purchased from AmBeed: ;

Ossowicz-Rupniewska, Paula ; Nowak, Anna ; Konopacki, Maciej , et al.

Abstract: A method of increasing the permeability of ibuprofen through the skin using a rotating magnetic field (RMF) is presented. This study evaluated whether 50 Hz RMF modifies ibuprofen′s permeability through the skin. Ibuprofen and its structural modifications in the form of ibuprofenates of iso-Pr esters of L-amino acids such as L-valine, L-phenylalanine, L-proline, and L-aspartic acid were used in the research. To this end, Franz cells with skin as membrane were exposed to 50 Hz RMF with 5% ibuprofen and its derivatives in an ethanol solution for 48 h. Following the exposures, the amount of penetrated compound was analyzed. Regardless of the compound tested, a significant increase in drug transport through the skin was observed The differences in the first 30 min of permeation are particularly noticeable. Furthermore, it was shown that using RMF increases the permeability of ibuprofen from 4 to 244 times compared to the test without the RMF. The greatest differences were observed for unmodified ibuprofen. However, it is noteworthy that the largest amounts of the active substance were obtained with selected modifications and exposure to RMF. The RMF may be an innovative and interesting technol. that increases the penetration of anti-inflammatory and anti-ache drugs through the skin.

Keywords: Electromagnetic field ; Rotating magnetic field ; Amino acid ; Nonsteroidal anti-inflammatory drugs ; Ibuprofen ; Transdermal drug delivery

Purchased from AmBeed:

Rakoczy, Rafal ; Nowak, Anna ; Konopacki, Maciej , et al.

Abstract: The paper presents a method of increasing the permeability of various active substances through the skin by means of a rotating magnetic field. The study used 50 Hz RMF and various active pharmaceutical ingredients (APIs) such as caffeine, ibuprofen, naproxen, ketoprofen, and paracetamol. Various concentrations of active substance solutions in ethanol were used in the research, corresponding to those in com. preparations Each experiment was conducted for 24 h. It was shown that, regardless of the active compound used, an increase in drug transport through the skin was observed with RMF exposure. Furthermore, the release profiles depended on the active substance used. Exposure to a rotating magnetic field has been shown to effectively increase the permeability of an active substance through the skin.

Keywords: Electromagnetic field ; Rotating magnetic field ; Active pharmaceutical ingredients ; Transdermal drug delivery ; Skin barrier

Purchased from AmBeed: ;

Agboola, Adebukola Abiola ; Nowak, Anna ; Duchnik, Wiktoria , et al.

DOI: PubMed ID:

Abstract: The aim of this study was to evaluate the effect of vehicle and chem. modifications of the structure of active compounds on the skin permeation and accumulation of ibuprofen (IBU). As a result, semi-solid formulations in the form of an emulsion-based gel loaded with ibuprofen and its derivatives, such as sodium ibuprofenate (IBUNa) and L-phenylalanine Et ester ibuprofenate ([PheOEt][IBU]), were developed. The properties of the obtained formulations were examined, including d., refractive index, viscosity, and particle size distribution. The parameters of release and permeability through the pig skin of the active substances contained in the obtained semi-solid formulations were determined The results indicate that an emulsion-based gel enhanced the skin penetration of IBU and its derivatives compared to two com. preparations in the form of a gel and a cream. The average cumulative mass of IBU after a 24 h permeation test from an emulsion-based gel formulation through human skin was 1.6-4.0 times higher than for the com. products. Ibuprofen derivatives were evaluated as chem. penetration enhancers. After 24 h of penetration, the cumulative mass was 1086.6 ± 245.8 for IBUNa and 948.6 ± 87.5 μg IBU/cm2 for [PheOEt][IBU], resp. This study demonstrates the perspective of the transdermal emulsion-based gel vehicle in conjunction with the modification of the drug as a potentially faster drug delivery system.

Keywords: carbomer ; increasing drug permeability ; nonsteroidal anti-inflammatory drugs ; ibuprofen ; transdermal drug delivery ; structural modification of ibuprofen

Purchased from AmBeed:

Nowak, Anna ; Ossowicz-Rupniewska, Paula ; Konopacki, Maciej , et al.

Abstract: This study introduces a novel approach for enhancing the transdermal permeability of through the skin by utilising a rotating magnetic field (RMF). The core objective is to systematically evaluate the influence of a 50 Hz RMF on ibuprofen’s skin permeability across various formulation types, each employing distinct physical forms and excipients. The experimental setup involved Franz cells with skin as the membrane, exposed to a 50 Hz RMF in conjunction with specific formulations. Subsequent comprehensive analysis revealed a notable increase in the transdermal transport of , irrespective of the formulation employed. Notably, the differences in the initial 30 min of permeation were particularly pronounced. Crucially, this investigation establishes that the application of a 50 Hz RMF resulted in a remarkable over-sevenfold increase in permeability compared to the control group without RMF exposure. It is noteworthy that in all semi-solid pharmaceutical formulations tested, RMF effectively reduced the delay time to zero, underscoring the efficiency of RMF in overcoming barriers to transdermal drug delivery. This research positions the application of RMF as a highly promising and innovative technology, significantly enhancing the transdermal penetration of anti-inflammatory and analgesic drugs through the skin. The demonstrated effectiveness of RMF across diverse formulations suggests its potential in transdermal drug delivery, offering a novel and efficient strategy for improving therapeutic outcomes in the administration of and potentially other pharmaceutical agents.

Keywords: electromagnetic field ; rotating magnetic field ; active pharmaceutical ingredients ; nonsteroidal anti-inflammatory drugs ; ; transdermal drug delivery ; skin barrier

Purchased from AmBeed:

Karolina Bilska ; Anna Nowak ; Anna Story , et al.

Abstract: This article presents a comprehensive study on the formulation andevaluation of pharmaceutical emulsions for topical drug delivery. Theresearch focused on emulsions containing ibuprofen and its derivatives(sodium and L-lysine propyl ester salts), investigating their solubility,consistency, stability, and skin permeation. The study offers valuableinsights into the development of effective pharmaceutical products.Background.Transdermal and topical drug delivery is a promisingapproach for the treatment of various medical conditions.Pharmaceutical emulsions provide an ideal platform for deliveringactive substances through the skin. The selection of emulsioningredients, consistency, and stability play a critical role in determiningthe suitability of these formulations. Aim of the study: The primary aim of this study was to formulate andevaluate pharmaceutical emulsions containing ibuprofen and otheractive substances. Key objectives included assessing the solubility,consistency, stability, and skin permeation characteristics of theemulsions. The study aimed to provide insights into the development ofeffective topical drug delivery systems. Material and methods: olubility tests were conducted to selectsuitable emulsion ingredients. Various emulsions were prepared withdifferent water-to-oil phase ratios. Rheology modifiers were added toenhance consistency. Quality control assessments were performedincluding uniformity, consistency, stability, density, viscosity, andparticle size analysis. The release of active substances from theformulations and their penetration and accumulation in the skin weredetermined. Results: The results revealed variations in viscosity, consistency, andstability among different formulations. Emulsion-based preparationsdemonstrated the highest accumulation of active substances in theskin, with formulation F1 (5294.617 yg/g skin) exhibiting the mostpromising results. The highest release of ibuprofen was observed inthe formulation based on Celugel with the addition of[LysOPr lBU (F6-approximately 7750 yg lBU/cm2, and the highest penetration of theactive substance was obtained for the emulsion with the addition ofIBU.Na (F2)-3300 yg lBU/cm2 after 24 hours of testing.Conclusion. This comprehensive study on pharmaceutical emulsionsfor topical drug delivery provides critical insights into the formulationand evaluation of cosmetic and pharmaceutical products. The findingshighlight the importance of ingredient selection, consistency, andstability in the development of effective emulsion-based formulationsFurthermore, the study suggests that emulsion-based preparationshave potential for topical applications, especially for more hydrophilicactive substances. Future research can build on these results toenhance drug delivery systems and improve patient outcomes.

Keywords: ibuprofen ; ibuprofenates of L-amino acid alkyl esters ; semi-solid pharmaceutical formulations ; skin permeability

Purchased from AmBeed:

Alternative Products

Product Details of [ 15687-27-1 ]

CAS No. :15687-27-1
Formula : C13H18O2
Linear Structure Formula :HO2CCH(CH3)C6H4CH2CH(CH3)2
M.W : 206.28
Synonyms :
DL-Ibuprofen;NSC 256857;Ibuprofen, Advil, Motrin, Nurofen, Brufen;U-18753;(±)-Ibuprofen
MDL No. :MFCD00010393
InChI Key :HEFNNWSXXWATRW-UHFFFAOYSA-N
Pubchem ID :3672

Safety of [ 15687-27-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H319-H335
Precautionary Statements:P261-P264-P539-P270-P271-P280-P301+P312+P330-P304+P340+P312-P305+P351+P338-P337+P313-P403+P233-P405-P501

Calculated chemistry of [ 15687-27-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 6
Fraction Csp3 0.46
Num. rotatable bonds 4
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 62.18
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

37.3 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.36
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.5
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.07
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

3.13
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.15
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.04

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.36
Solubility 0.0909 mg/ml ; 0.000441 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.97
Solubility 0.0223 mg/ml ; 0.000108 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.44
Solubility 0.0749 mg/ml ; 0.000363 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.07 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 1.92

Application In Synthesis [ 15687-27-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 15687-27-1 ]

[ 15687-27-1 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 15687-27-1 ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
YieldReaction ConditionsOperation in experiment
With ammonium acetate; In hexane; isopropyl alcohol;Resolution of racemate;Purification / work up; Enantiomers of test racemates TR 19-23, of known drugs from the non-steroidal antiinflammatory group, were separated on analytical HPLC columns (250 mm x 4,6 mm), filled with CSP-4 or CSP-3. Since these compounds are structurally free carboxyl acids, it was necessary to use a polar mobile phase containing a certain amount of ammonium acetate. Results obtained by the enantioselective separation of these compounds are shown in Table 5 and the chromatogram achieved for the enantiomers of naproxen is shown in Figure 8. <n="20"/>TABLE 5 Enantiomer separations for test racemate TR 20-23 on the column filled withCSP-3 (250 mm x 4.6 mm ID), with hexane : 2-PrOH = 8:2 + lg/L NH4OAc as the mobile phase, 1 ml/min, 254 nm.
With 2C8H8N5O2(1-)*Cu(2+); In hexane; at 60℃;Resolution of racemate;Catalytic behavior; Prior to analysis, the MOFs having repeating units of (SS)-(IA1) of the invention was prepared from the MOFs having repeating units of (SS)-(IBI ') by activation. Particularly, MOFs having repeating units of (SS)-(IBI ') was activated in vacuum at 150C for 12 h on a Schlenk line. 30 mg of the activated MOF having repeating units of (SS)-(IA1) was placed into a solvent as defined in Table 8 at the appropriate temperature as shown in Table 8 with racemic ibuprofen (50% S/R) in a molar ratio (SS)- (IA1):ibuprofen of 1 :3. The reaction was stirred at the temperature indicated in Table 8 overnight. The reaction was filtered to remove the solid, which was washed with a small amount of fresh acetonitrile to remove any ibuprofen sorbed on the surface of the framework. The term "mother liquor" refers to the mixture of the filtrate and the first wash. he amount and chirality of ibuprofen sorbed by the activated MOF was extracted from the solid by suspension in CHCI3 (2 ml) at room temperature for 1 hour. After this time the solid was removed by filtration and the filtrate was analysed by 1H NMR. The enantiomeric excess was determined comparing with the commercially available pure enantiomer, (S)- (+)-lbuprofen or (S)-(+)-4-lsobutyl-a-methylphenylacetic acid, or (S)-(+)-2-(4-lsobutylphenyl)propionic acid (CAS: 51146-56-6, Sigma-Aldrich); and (R)-(+)-lbuprofen or (R)-(+)-4-lsobutyl-a-methylphenylacetic acid or (R)-(+)-2-(4-lsobutylphenyl)propionic acid (CAS: 51146-57-7, Santa Cruz Bio Biotech) using a ultra- performance convergence chromatography (UPPC), ACQUITY UPC2 Waters system with Diode Array Detector; a Column: ChiralPak IA 4.6mm x 100mm, 3mueta, under the following conditions: CO2/ACN/TFA 88:12:0.5, 3ml/min, 1500 psi. Table 8 summarizes the amount of each one of the enantiomer of ibuprofen in the mother liquor and also in the ibuprofen extracted from the MOFs having repeating units of (SS)-(IA1) of the in the invention. Furthermore, Table 8 also specifies the solvent and the temperature of each one of the independent runs:
With colistin sulfate-based polymer monolithic column; In methanol; water; at 20℃;Resolution of racemate; Green chemistry; General procedure: The colistin sulfate-based polymer monolithic capillary column was prepared as describedabove and investigated for the nano-LC enantioseparation of a set of different classes of racemicpharmaceuticals, namely: beta-blockers, alpha-blockers, anti-inflammatory drugs, antifungal drugs,norepinephrine-dopamine reuptake inhibitors, catecholamines, sedative hypnotics, antihistamines,antibacterial drugs, anticancer drugs and antiarrhythmic drugs. Although reversed phaseenantio-selective LC examples are limited, macrocyclic antibiotics were previously used inenantioseparation chromatography under reversed phase chromatographic mode [34,36-38,42-45].The initial mobile phase selected for the enantioseparation separation of racemates 1-37 (Figure 3) wasa binary mixture of methanol/water screened from 95:5 to 5:95 nu/nu at 1 mL/min flow rate at fixed UVdetection 219 nm with eleven compounds separated (Rs 1) (Table 1). For examples, in MeOH/H2O80:20 nu/nu, only ibuprofen (7) was separated, while in MeOH/H2O 40:60, indoprofen (10), hexaconazole(15) and miconazole (16) were separated. In MeOH/H2O 10:90 nu/nu, aminoglutethimide (22), tyrosine(29) and O-methoxymandelic acid (34) were also separated. The addition of an additive, namelytriethylamine (TEA) 1% nu/nu in 10:90, resulted in the separation of acebutolol (4) normetanephrine(21), propafenone (26), tyrosine (29) and 4-hydroxy-3-methoxymandelic acid (35) (Figure 4), whilenon-acceptable separations were achieved by addition of the acidic additive namely trifluoroaceticacid (TFA). In an attempt to use normal phase namely n-hexane/2-propanol mixture ranging from10-90% (nu/nu) resulted in resolution less than 1. All chromatographic data are summarized in Table 1.
  • 2
  • [ 6265-73-2 ]
  • [ 15687-27-1 ]
  • [ 761415-91-2 ]
  • 3
  • [ 71-23-8 ]
  • [ 15687-27-1 ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
  • (R)-ibuprofen 1-propyl ester [ No CAS ]
  • 5
  • [ 934343-41-6 ]
  • [ 50-00-0 ]
  • [ 6642-30-4 ]
  • [ 15687-27-1 ]
  • 6
  • [ 15687-27-1 ]
  • [ 84500-41-4 ]
  • [ 852055-78-8 ]
YieldReaction ConditionsOperation in experiment
95.3% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 19h; (+)-Ibuprofen (4.15 g, 20.11 mmole), N-carbobenzyloxy-L-threonine benzyl ester (6.90 g, 20.11 mmole), 1- (3-dimethylaminopropyl)-3-ethylcarbodiimide, hydrochloride (EDC, 3.95 g, 20.6 mmole), and 4-(N, N-dimethylamino)-pyridine (DMAP, 0.25 g, 2.0 mmole) were dissolved in dichloromethane (50 mL) at room temperature, under an argon atmosphere. After stirring for 19 hours, the dichloromethane layer was washed with water (50 mL), 5% hydrochloric acid (2x25 mL), water (25 mL), saturated sodium bicarbonate (2x25 mL), and water (50 mL). After drying for one hour over sodium sulfate (5 g), filtration, and concentration under reduced pressure, the remaining oil was used without further purification. The procedure generated the protected L-threonine- ()-Ibuprofen ester (SPI001601) as a light yellow oil (10.2 g, 95.3% yield), which solidified on standing. 2 (S)-Benzyloxycarbonylamino-3- [2 (R, S)- (4-isobutyl-phenyl)-propionyloxy]-butyric acid benzyl ester: 'H NMR (300 MHz, CDC13) : a = 7.40-7. 15 (m, 10H), 7.14-7. 01 (m, 4H), 5.48-5. 25 (m, 2H), 5.11-5. 01 (m, 3H), 4.90 (d, 1/2H, J= 12 Hz), 4.68 (d, l/2H, J= 12 Hz), 4.48 (m, 1H), 3.60-3. 48 (m, 1H), 2.39 (m, 2H), 1.79 (m, 1H), 1.42-1. 35 (m, 3H), 1.27 (d, 1.5 H, J= 6. 6 Hz), 1.17 (d, 1.5 H, J= 6.6 Hz), 0. 85 (m, 6 H). 3C NMR (75 MHz, CDC13) : 8 = 173. 32,169. 70,169. 30,156. 55,140. 75,137. 38, 137.22, 136.14, 135.07, 134.99, 129.45, 129.41, 128.65, 128.39, 128.22, 127.21, 127.14, 70.97, 70.70, 67.81, 67.66, 67.53, 57.83, 45.19, 30.39, 22.61, 18.57, 18.30, 17.18, 16.87
  • 7
  • [ 15687-27-1 ]
  • [ 62784-66-1 ]
  • [ 1116086-46-4 ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
YieldReaction ConditionsOperation in experiment
39% With p-Methoxybenzoic anhydride; N-ethyl-N,N-diisopropylamine;(R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In dichloromethane; at 20℃; for 12h;Resolution of racemate; Entry 44To a dichloromethane solution (1.0 mL) containing p-methoxybenzoic anhydride (68.9 mg, 0.241 mmol) and racemic ibuprofen (41.2 mg, 0.200 mmol); diisopropylethylamine (62.7 muL, 0.360 mmol), benzotetramisole (2.5 mg, 0.010 mmol), and 1,1-di(1-naphthyl)methanol (28.4 mg, 0.100 mmol) were added in order at room temperature. After stirring the reaction mixture solution at room temperature for 12 hr, the reaction was stopped with saturated ammonium chloride water. After fractionating the organic layer, the aqueous layer was extracted 4 times with diethylether. After combining the organic layers, they were dried with anhydrous sodium sulfate. After filtering the solution, it was vacuum concentrated, and the obtained mixture was fractionated by thin layer silica gel chromatography to obtain the corresponding optically active ibuprofen ester (36.9 mg, 39percent, 92percent ee) and the unreacted optically active ibuprofen (13.6 mg, 33percent, 36percent ee).(R)-ibuprofen di(1-naphthyl)methylesterHPLC (CHIRALPAK AD-H, i-PrOH/hexane=1/9, flow rate=1.0 mL/ml): tR=6.1 min (4.1percent), tR=10.7 min (95.9percent);IR (neat): 3036, 1735, 1599, 1512, 782, 679 cm-1;1H NMR (CDCl3): delta8.29 (s, 1H, 1-H), 8.02-7.93 (m, 1H, Ph), 7.85-7.60 (m, 5H, Ph), 7.47-7.26 (m, 3H, Ph), 7.24-7.02 (m, 6H, Ph), 7.00-6.88 (m, 3H, Ph), 3.74 (q, J=7.1 Hz, 1H, 2-H), 2.38 (d, J=7.1 Hz, 2H, 1'-H), 1.78 (qq, J=6.6, 6.6 Hz, 1H, 2'-H), 1.43 (d, J=7.1 Hz, 3H, 3-H), 0.84 (d, J=6.6 Hz, 6H, 3'-H);13C NMR (CDCl3): delta173.7, 140.6, 137.2, 134.9, 134.7, 133.8, 133.7, 131.2, 130.9, 129.3, 129.1, 128.8, 128.7, 128.6, 127.5, 126.7, 126.3, 125.8, 125.6, 125.2, 125.0, 123.5, 123.4, 70.9, 45.3, 45.0, 30.2, 22.4, 18.1;HR MS: calculated for C34H32O2Na (M+Na+)=495.2295; found 495.2276.(S)-ibuprofenHPLC (CHIRALPAK AD-H, i-PrOH/hexane/TFA=1/100/0.1, flow rate=1.0 mL/min); tR=26.3 min (77.5percent), tR=28.5 min (22.5percent);1H NMR (CDCl3): delta10.30 (br s, 1H, COOH), 7.14 (d, J=7.9 Hz, 2H, Ph), 7.02 (d, J=7.9 Hz, 2H, Ph), 3.63 (q, J=7.3 Hz, 1H, 2-H), 2.37 (q, J=7.3 Hz, 2H, 1'-H), 1.77 (qq, J=6.5, 6.5 Hz, 1H, 2'-H), 1.42 (d, J=7.3 Hz, 2H, 3-H), 0.82 (d, J=6.5 Hz, 6H, 3'-H).
  • 8
  • [ 15687-27-1 ]
  • [ 62784-66-1 ]
  • [ 1224446-49-4 ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
  • 9
  • [ 15687-27-1 ]
  • [ 110282-71-8 ]
  • [ 1187670-13-8 ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
YieldReaction ConditionsOperation in experiment
36% With benzoic acid anhydride; N-ethyl-N,N-diisopropylamine;(R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In dichloromethane; at 20℃; for 6h;Resolution of racemate; Experimental Example 6Production of Optically Active Ester and Optically Active Carboxylic Acid Using Ibuprofen (Optical Resolution of Ibuprofen) As shown by the above reaction equation, an optically active ester and optically active carboxylic acid are obtained by reacting 1,1-di(1-naphthyl)methanol or 1,1-di(9-phenanthryl)methanol and racemic ibuprofen. The results are shown in Table 6. ; Entry 46(R)-ibuprofen di(9-phenanthryl)methylesterHPLC (CHIRALPAK AD-H, i-PrOH/hexane=1/50, flow rate=0.5 mL/ml): tR=18.4 min (5.6percent), tR=24.9 min (94.4percent);IR (KBr): 3068, 1732, 1451, 1155, 750, 726 cm-1;1H NMR (CDCl3): delta8.83-8.60 (m, 4H, Ph), 8.40 (s, 1H, 1-H), 8.18-8.09 (m, 1H, Ph), 7.82-7.04 (m, 17H, Ph), 3.89 (q, J=7.2 Hz, 1H, 2-H), 2.61-2.45 (m, 2H, 1'-H), 2.00-1.81 (m, 1H, 2'-H), 1.55 (d, J=7.2 Hz, 3H, 3-H), 0.95 (d, J=6.6 Hz, 6H, 3'-H);13C NMR (CDCl3): delta173.7, 133.0, 132.7, 131.1, 131.0, 130.9, 130.6, 130.6, 130.4, 130.2, 129.8, 129.5, 129.1, 127.9, 127.5, 127.3, 127.2, 127.0, 126.9, 126.9, 126.6, 126.4, 126.2, 124.3, 123.9, 123.3, 123.1, 122.4, 122.4, 70.8, 45.3, 45.1, 30.2, 22.5, 22.4, 18.2.
  • 10
  • [ 15687-27-1 ]
  • [ 110282-71-8 ]
  • [ 1187670-13-8 ]
  • (S)-ibuprofen di(9-phenanthryl)methyl ester [ No CAS ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
YieldReaction ConditionsOperation in experiment
With p-Methoxybenzoic anhydride; N-ethyl-N,N-diisopropylamine;(R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In dichloromethane; at 20℃; for 12h;Resolution of racemate; Experimental Example 6Production of Optically Active Ester and Optically Active Carboxylic Acid Using Ibuprofen (Optical Resolution of Ibuprofen) As shown by the above reaction equation, an optically active ester and optically active carboxylic acid are obtained by reacting 1,1-di(1-naphthyl)methanol or 1,1-di(9-phenanthryl)methanol and racemic ibuprofen. The results are shown in Table 6. ; Entry 46(R)-ibuprofen di(9-phenanthryl)methylesterHPLC (CHIRALPAK AD-H, i-PrOH/hexane=1/50, flow rate=0.5 mL/ml): tR=18.4 min (5.6percent), tR=24.9 min (94.4percent);IR (KBr): 3068, 1732, 1451, 1155, 750, 726 cm-1;1H NMR (CDCl3): delta8.83-8.60 (m, 4H, Ph), 8.40 (s, 1H, 1-H), 8.18-8.09 (m, 1H, Ph), 7.82-7.04 (m, 17H, Ph), 3.89 (q, J=7.2 Hz, 1H, 2-H), 2.61-2.45 (m, 2H, 1'-H), 2.00-1.81 (m, 1H, 2'-H), 1.55 (d, J=7.2 Hz, 3H, 3-H), 0.95 (d, J=6.6 Hz, 6H, 3'-H);13C NMR (CDCl3): delta173.7, 133.0, 132.7, 131.1, 131.0, 130.9, 130.6, 130.6, 130.4, 130.2, 129.8, 129.5, 129.1, 127.9, 127.5, 127.3, 127.2, 127.0, 126.9, 126.9, 126.6, 126.4, 126.2, 124.3, 123.9, 123.3, 123.1, 122.4, 122.4, 70.8, 45.3, 45.1, 30.2, 22.5, 22.4, 18.2.
  • 11
  • [ 15687-27-1 ]
  • [ 62784-66-1 ]
  • [ 1116086-46-4 ]
  • [ 1224446-49-4 ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
YieldReaction ConditionsOperation in experiment
With benzoic acid anhydride; N-ethyl-N,N-diisopropylamine;(R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In dichloromethane; at 20℃; for 6h;Resolution of racemate; Experimental Example 6Production of Optically Active Ester and Optically Active Carboxylic Acid Using Ibuprofen (Optical Resolution of Ibuprofen) As shown by the above reaction equation, an optically active ester and optically active carboxylic acid are obtained by reacting 1,1-di(1-naphthyl)methanol or 1,1-di(9-phenanthryl)methanol and racemic ibuprofen. The results are shown in Table 6.; R)-ibuprofen di(1-naphthyl)methylesterHPLC (CHIRALPAK AD-H, i-PrOH/hexane=1/9, flow rate=1.0 mL/ml): tR=6.1 min (4.1percent), tR=10.7 min (95.9percent);IR (neat): 3036, 1735, 1599, 1512, 782, 679 cm-1;1H NMR (CDCl3): delta8.29 (s, 1H, 1-H), 8.02-7.93 (m, 1H, Ph), 7.85-7.60 (m, 5H, Ph), 7.47-7.26 (m, 3H, Ph), 7.24-7.02 (m, 6H, Ph), 7.00-6.88 (m, 3H, Ph), 3.74 (q, J=7.1 Hz, 1H, 2-H), 2.38 (d, J=7.1 Hz, 2H, 1'-H), 1.78 (qq, J=6.6, 6.6 Hz, 1H, 2'-H), 1.43 (d, J=7.1 Hz, 3H, 3-H), 0.84 (d, J=6.6 Hz, 6H, 3'-H);13C NMR (CDCl3): delta173.7, 140.6, 137.2, 134.9, 134.7, 133.8, 133.7, 131.2, 130.9, 129.3, 129.1, 128.8, 128.7, 128.6, 127.5, 126.7, 126.3, 125.8, 125.6, 125.2, 125.0, 123.5, 123.4, 70.9, 45.3, 45.0, 30.2, 22.4, 18.1;HR MS: calculated for C34H32O2Na (M+Na+)=495.2295; found 495.2276.(S)-ibuprofenHPLC (CHIRALPAK AD-H, i-PrOH/hexane/TFA=1/100/0.1, flow rate=1.0 mL/min); tR=26.3 min (77.5percent), tR=28.5 min (22.5percent);1H NMR (CDCl3): delta10.30 (br s, 1H, COOH), 7.14 (d, J=7.9 Hz, 2H, Ph), 7.02 (d, J=7.9 Hz, 2H, Ph), 3.63 (q, J=7.3 Hz, 1H, 2-H), 2.37 (q, J=7.3 Hz, 2H, 1'-H), 1.77 (qq, J=6.5, 6.5 Hz, 1H, 2'-H), 1.42 (d, J=7.3 Hz, 2H, 3-H), 0.82 (d, J=6.5 Hz, 6H, 3'-H).
  • 12
  • [ 64-17-5 ]
  • [ 15687-27-1 ]
  • [ 51146-57-7 ]
  • [ 272458-63-6 ]
  • 13
  • [ 56-87-1 ]
  • [ 15687-27-1 ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
  • (S)-(+)-ibuprofen (S)-lysinate [ No CAS ]
  • 14
  • [ 15687-27-1 ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
  • (R)-ibuprofen 1-propyl ester [ No CAS ]
  • 15
  • [ 71-23-8 ]
  • [ 15687-27-1 ]
  • [ 51146-57-7 ]
  • (S)-ibuprofen 1-propyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Candida rugosa lipase immobilized on octyl sepharose; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; at 40℃; for 120h;Molecular sieve; Resolution of racemate; Enzymatic reaction; In a 15ml reaction vial, the appropriate racemic acid (0.05mmol) and n-propanol (0.15mmol), were dissolved in 5ml organic solvent (isooctane) or ionic liquids ([BMIM]BF4 or [BMIM]PF6) in presence of molecular sieves (Scheme 1). The mixture was stirred and heated at 40°C. Thereafter, 50muL of the samples were withdrawn and injected at zero time (control). The immobilized enzymes (20mg) were added and 50muL sample of the supernatant was withdrawn and directly injected to GC without dilution or workup at several time intervals.
  • 16
  • [ 71-23-8 ]
  • [ 15687-27-1 ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
  • (S)-ibuprofen 1-propyl ester [ No CAS ]
  • 17
  • [ 71-23-8 ]
  • [ 15687-27-1 ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
  • (S)-ibuprofen 1-propyl ester [ No CAS ]
  • (R)-ibuprofen 1-propyl ester [ No CAS ]
  • 18
  • [ 15687-27-1 ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
  • [ 114937-30-3 ]
  • 19
  • [ 31469-22-4 ]
  • [ 2051-99-2 ]
  • [ 15687-27-1 ]
 

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Chemical Structure| 1216459-54-9

A1230249[ 1216459-54-9 ]

Ibuprofen-(ring-13C6)

Reason: Stable Isotope