成人免费xx,国产又黄又湿又刺激不卡网站,成人性视频app菠萝网站,色天天天天

Home Cart Sign in  
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 534-03-2 Chemical Structure| 534-03-2

Structure of 534-03-2

Chemical Structure| 534-03-2

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

{[proInfo.proName]}

CAS No.: 534-03-2

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Product Citations

Surmiak, Ewa ; Zaber, Julia ; Plewka, Jacek ; Wojtanowicz, Grzegorz ; Kocik-Krol, Justyna ; Kruc, Oskar , et al.

Abstract: Although heavily studied, the subject of anti-PD-L1 small-mol. inhibitors is still elusive. Here, we present a systematic overview of the principles behind the successful anti-PD-L1 small mol. inhibitor design on the example of the m-terphenyl scaffold with a particular focus on the neglected influence of the solubilizer tag on the overall affinity toward PD-L1. The inhibitor developed according to the proposed guidelines was characterized through its potency in blocking the PD-1/PD-L1 complex formation in HTRF and cell-based assays. The affinity is also explained based on the crystal structure of the inhibitor itself, its costructure with PD-L1 as well as mol. modeling study. Our results structuralize the knowledge related to the strong pharmacophore feature of the m-terphenyl scaffold preferential geometry and the more complex role of the solubilizer tag in PD-L1 homodimer stabilization.

Keywords: PD-L1 ; Immune checkpoint ; Small-molecule inhibitor ; Cancer ; m-Terphenyl

Purchased from AmBeed: ; 534-03-2

Alternative Products

Product Details of [ 534-03-2 ]

CAS No. :534-03-2
Formula : C3H9NO2
M.W : 91.11
SMILES Code : OCC(N)CO
MDL No. :MFCD00051487
InChI Key :KJJPLEZQSCZCKE-UHFFFAOYSA-N
Pubchem ID :68294

Safety of [ 534-03-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P501-P260-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405
Class:8
UN#:3259
Packing Group:Ⅲ

Computational Chemistry of [ 534-03-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 6
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 3.0
Molar Refractivity 21.57
TPSA ?

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

66.48 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

0.73
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

-2.02
Log Po/w (WLOGP)?

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

-1.7
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.

-1.51
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

-1.2
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-1.14

Water Solubility

Log S (ESOL):?

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

1.0
Solubility 911.0 mg/ml ; 9.99 mol/l
Class?

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

Highly soluble
Log S (Ali)?

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

1.15
Solubility 1280.0 mg/ml ; 14.1 mol/l
Class?

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

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

0.87
Solubility 669.0 mg/ml ; 7.35 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

 No
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.

-8.29 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

 3.0
Bioavailability Score?

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

0.55

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)

 1.0

Application In Synthesis of [ 534-03-2 ]

* 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 [ 534-03-2 ]

[ 534-03-2 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 24424-99-5 ]
  • [ 534-03-2 ]
  • [ 125414-41-7 ]
YieldReaction ConditionsOperation in experiment
100% In ethanol; at 20℃; for 16h; To a solution of 2-anunopropane-1 ,3-diol (1 0. 0 g, 0.1 mol) in EtOH ( 100 mL) wasadded di-tert-butyl dicarbonate (24.0 g, 0.1 mol). The reaction was stirred at room temperaturefor 16 hrs. The reaction solution was concentrated in vacuo to dryness to give tert-butyl (1,3-dihydroxypropan-2-yl)carbamate (21.0 g, yield: 1 00'%) as a white solid.
97% In dichloromethane; at 22 - 25℃; for 4h; Serinol (2.00 g, 21.96 mmol) and (Boc)20 (4.80 g, 21.96 mmol) was dissolved in 20 mL of dichloromethane. The reaction mixture was stirred for 4 h at 22 to 25 C. The above mixture was washed with water (25 mL x 2), dried over anhydrous sodium sulfate and concentrated under vacuum toyield tert-butyl (1 ,3-dihydroxypropan-2-yl)carbamate (4.1 g, 97% yield).
95% With hydrogenchloride; In 1,4-dioxane; water; at 20℃;Cooling with ice; Serinol (10.1 mmol) (manufactured by Aldrich Chem. Co.) was dissolved in water-dioxane (1:1, 20 ml), andthen a dioxane solution (15 ml) of Boc2O (10.8 mmol) was added thereto under ice-cooling, followed by stirring overnightwhile returning to room temperature. The solvent was evaporated under reduced pressure. The residue was washedwith hexane and then dried under reduced pressure to give the titled compound (1847 mg, yield 95%).The structurewas identified by 1H-NMR.1H-NMR (500 MHz, CD3OD) delta (ppm) = 1.44 (9H, s, Boc), 3.57-3.58 (5H, m, Serinol)
95% With trimethylamine; In dichloromethane; for 4h; Serinoi (2,00 g, 22,0 mmol) was dissolved in dichioromethane (40 mL) and trimethylamitie (10 mL). Di-tert-butyl dicarbonate (5.76 g, 26.4 mmol, 1.2 eq) was then added, and the reaction stirred for 4 hours. The mixture was evaporated and the residue portioned between ethyl acetate and water. The organic fraction was washed with water ( lx), 1M HC1 (2x), saturated sodium bicarbonate (lx), and brine (lx) before drying over sodium sulfate and evaporation to give compound 23 (3.99 g, 20.9 mmol) in 95% yield, which was used without purification in further steps.
91% In ethanol; at 20℃; for 6h; 2-amino-1,3-propanediol (5 g) was dissolved in 150 mL of absolute ethanol, A solution of 100 mL of Boc anhydride (12 g) in absolute ethanol was added, Room temperature reaction 6h, Remove the solvent, Recrystallization from n-heptane gave a white solid 3 (9.6 g, 91%).
72% With N-ethyl-N,N-diisopropylamine; In methanol; for 0.25h;Product distribution / selectivity; Example 2Lambda/-Boc-Serinol. Lambda/,Lambda/-diisopropylethylamine (DIEA; 10.3 ml_, 59 mmol, 1.1 equiv) was added to serinol (4.88 g, 54 mmol, 1 equiv) in 10 ml_ methanol. A solution of di-f-butyl dicarbonate (12.9 g, 59 mmol, 1.1 equiv.) in 5 mL methanol was then added to the original solution. The reaction was exothermic and evolved gas. The reaction appeared to be complete after 15 min. (as determined by TLC analysis in 9:1 CHCI3:CH3OH with ninhydrin stain). The solvent was then removed at reduced pressure, and the crude material was purified by flash chromatography, using CHCI3:CH3OH (first at a 9:1 ratio and then at a 85:15 ratio), to yield 7.18g (72% yield) of white, flaked crystals. [Rf: 0.35 (5:1 CHCI3:CH3OH); melting point 85-860C; 1H NMR (200 MHz, CDCI3) delta 5.25 (br d, J = 5.6, 1 H, NH), 3.9-3.65 (m, 5H, (-CH2)2CH-), 2.62 (t, J = 5.6, 2H, OH), 1.45 (s, 9H, C(CHa)3)]. EPO <DP n="30"/>Example 3[0107] To prepare the bis-phthalonitrile used in scheme 2, the nitrogen of serinol was Boc-protected, and the serinol was then reacted with 3-nitrophthalonitrile on a multi-gram scale, to give the desired tethered bis-phthalonitrile, in 70% yield
62% With potassium carbonate; In tetrahydrofuran; water; at 20℃; 2-Amino-1,3-propanediol (1.62 g, 17.8 mmol, 1.0 eq) was dissolved in 60 mL of tetrahydrofuran/H2O (1/1). Di-tert-butyl dicarbonate (Boc2O) (5.82 g, 26.7 mmol, 1.5 eq) and K2CO3 (6.15 g, 44.5 mmol,2.5 eq) were added. The reaction was stirred at room temperature overnight. The reaction systemwas allowed to stand for stratification, and the aqueous phase was extracted three times withtetrahydrofuran. The organic phase was combined, dried over anhydrous Na2SO4, evaporatedin vacuo, and puried by column chromatography (silica gel:petroleum ether/ethyl acetate, 1:1) toproduce compound 4 as a white solid in a 62% yield (2.1 g, 11.0 mmol). 1H-NMR (400 MHz, CDCl3) 5.24 (s, 1H), 3.81 (qd, J = 11.1, 4.3 Hz, 4H), 3.69 (s, 1H), 2.50 (dd, J = 22.1, 14.7 Hz, 2H), 1.46 (s, 9H),which agrees with published data [39].
49% With triethylamine; In tetrahydrofuran; at 0 - 20℃; 2-Amino-1 ,3-propanediol (5.Og, 54.9mmol) was dissolved in dry THF (175ml) and triethylamine (7.7ml) added. The solution was cooled in an ice-bath and di-fe/f- butylcarbonate (11.98g, 54.9mmol) added in portions over 15mins. The solution was allowed to warm to ambient temperature and stirred for 90mins. The solvent was evaporated and water (250ml) added and the product extracted into ethyl acetate (4 x 125ml). The combined organics were washed with brine, dried over magnesium sulphate, filtered and evaporated. The product was isolated by recrystallization from hot ethyl acetate-petrol (1 :3) to give shiny flakes 5.18g (49% yield). The structure was confirmed by 1H NMR (300MHz , CDCI3): 1.44 (s, 9H), 3.08-3.17 (m, 1 H), 3.61 - 3.84 (m, 4H).
With triethylamine; In dichloromethane; at 20℃;Cooling with ice; General procedure: Diols or diamine (0.048 mol) and triethylamine (4.81 g, 0.057 mol) were dissolved in anhydrous CH2Cl2 (50 mL). (Boc)2O (12.45 g, 0.057 mol) in anhydrous CH2Cl2 solution was added dropwise to the above stirred solution under the ice bath. The mixture was stirred overnight at room temperature, followed by evaporation of the organic solvents. The residue was purified with silica gel column chromatography (dichloromethane/methyl alcohol = 30: 1). The synthesis of naked two primary amine compound according to the literature [29]. Then, acryloyl chloride (6.95 g, 0.077 mol) in anhydrous dichloromethane (50 mL) was added dropwise to a stirred solution of diol or diamine (0.038 mol) and triethylamine (7.77 g, 0.077 mol) in anhydrous dichloromethane (50 mL) under the ice bath. The mixture was stirred overnight at room temperature and then filtered off generated salt, followed by evaporation of the volatile solvent. The residue was purified with silica gel column chromatography (PE: EA = 3: 1, v/v) to give LC1-LC6.
With triethylamine; In dichloromethane; at 0 - 20℃; General procedure: Diethanolamine 3 (or threoninol 5, 3-amino-1,2-propanediol 6)(0.047 mol) was dissolved in CH2Cl2 and triethylamine (9.60 g,0.095 mol) was slowly added. The solution was cooled to 0 C,and (Boc)2O (12.45 g, 0.057 mol) was added dropwise. Then themixed solution was left for stirring at room temperature overnight.The solvent was removed under reduce pressure to afford crudeproduct, which was further purified by silica gel column chromatography(CH2Cl2/CH3OH = 10/1, v/v) to give compound 3a (or5a, 6a).
With triethylamine; In dichloromethane; Referring to Scheme LLL, the amino group in diol 1-29 is protected with Boc2O to provide compound 1-30 which is mesylated (e.g., with MsC1 and TEA) to afford compound 1-31. Compound 1-31 is subjected to a double nucleophilic substitution with pyrazolone 1-9, providing1-32, which is brominated (e.g., with NBS) to afford compound 1-33. Sequential treatment of 1-33 with n-butyl lithium, zinc chloride, and TCPC provides compound 1-34. Intermediate 61 is obtained when 1-34 is reacted with aqueous ammonia.
In methanol; water; at 0 - 25℃; for 4.5h; Add 6mL of deionized water and 14mL of methanol to the three-necked flask, stir and mix well, then add 0.02mol serinol to the mixed solution, stir and dissolve it completely, cool to 0 C with an ice bath, and then add the three mixed solutions Slowly add 0.022mol of di-tert-butyl dicarbonate. During the dropwise addition, the temperature was maintained at 0 C. After 30 minutes, the ice bath was removed and the reaction was performed at a constant 25 C for 4 hours. After the reaction was completed, extraction was performed three times with dichloromethane. The solvent methanol and water were distilled off under reduced pressure, and vacuum-dried at 45 C. for 24 h to obtain the product tert-butyl 1,3-dihydroxypropane-2-carbamate.
With triethylamine; In dichloromethane; for 4h; Serinol (2.00 g, 22.0 mmol) was dissolved in dichloromethane (40 mL) and trimethyamine ( 10 mL). Di-tert-butyl dicarbonate (5.76 g, 26.4 mmol, 1 .2 eq) was then added, and the reaction stirred for 4 hours. The mixture was evaporated and the residue portioned between ethyl acetate and water. The organic fraction was washed with water ( l x), 1 M HCI (2x), saturated sodium bicarbonate ( l x), and brine ( l x) before drying over sodium sulfate and evaporation to give compound 23 (3.99 g, 20.9 mmol) in 95% yield, which was used without purification in further steps.

References: [1]Tetrahedron Letters,2007,vol. 48,p. 8318 - 8322.
[2]Patent: WO2018/136890,2018,A1 .Location in patent: Paragraph 0729; 00730; 00801; 00802.
[3]Patent: WO2015/79459,2015,A1 .Location in patent: Paragraph 00296.
[4]Advanced Synthesis and Catalysis,2003,vol. 345,p. 835 - 848.
[5]Patent: EP3363463,2018,A2 .Location in patent: Paragraph 0153.
[6]Patent: WO2019/199621,2019,A1 .Location in patent: Page/Page column 91-92.
[7]Synthesis,1998,p. 1113 - 1118.
[8]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2086 - 2090.
[9]Tetrahedron,2009,vol. 65,p. 8393 - 8401.
[10]Molecular Pharmaceutics,2018,vol. 15,p. 5479 - 5492.
[11]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 3832 - 3835.
[12]Patent: CN106554378,2017,A .Location in patent: Paragraph 0041; 0042.
[13]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 2205 - 2212.
[14]Tetrahedron Asymmetry,2002,vol. 13,p. 2197 - 2199.
[15]Organic Letters,2013,vol. 15,p. 6094 - 6097.
[16]Chemistry - A European Journal,2011,vol. 17,p. 895 - 904.
[17]RSC Advances,2014,vol. 40,p. 41588 - 41596.
[18]Organic Letters,2007,vol. 9,p. 215 - 218.
[19]Patent: WO2007/9101,2007,A2 .Location in patent: Page/Page column 22; 27; 28.
[20]Molecules,2019,vol. 24.
[21]Chemistry - A European Journal,2019,vol. 25,p. 6831 - 6839.
[22]Patent: WO2009/47319,2009,A1 .Location in patent: Page/Page column 27.
[23]Journal of the American Chemical Society,2004,vol. 126,p. 4329 - 4342.
[24]Synthesis,1989,p. 256 - 261.
[25]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5900 - 5903.
[26]RSC Advances,2013,vol. 3,p. 6771 - 6774.
[27]Polymer,2015,vol. 65,p. 45 - 54.
[28]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 5756 - 5763.
[29]RSC Advances,2018,vol. 8,p. 37715 - 37723.
[30]Patent: WO2019/79119,2019,A1 .Location in patent: Page/Page column 532; 536.
[31]Journal of Pharmaceutical Sciences,2019,vol. 108,p. 3074 - 3081.
[32]Patent: CN107043620,2019,B .Location in patent: Paragraph 0017-0019; 0026-0028; 0035-0037.
[33]Patent: WO2019/199634,2019,A1 .Location in patent: Page/Page column 70; 97.
  • 2
  • [ 66127-01-3 ]
  • [ 534-03-2 ]
  • [ 321595-65-7 ]
  • 3
  • [ 60166-91-8 ]
  • [ 534-03-2 ]
  • [ 60166-93-0 ]
YieldReaction ConditionsOperation in experiment
94% In ISOPROPYLAMIDE; at 8 - 20℃; for 10h; 680 g of S-(-)-5-((2-acetyloxy)-1-oxopropyl)amino)-2,4,6-triiodo-1,3-benzendicarboxylic acid dichloride (prepared as described in WO 96/37460) are dissolved in 1360 g of dimethylacetamide at room temperature and after cooling at 15C [Solution A ]. 181 g of 2-ammino-1,3-propanediol purified with the method described in the previous Example 1 are dissolved in 1360 g of dimethylacetamide and added to the solution A in one hour at 8-15C whilst stirring. The reaction is completed after ten hours at room temperature. The reaction mixture is concentrated at 100C at 10 mbar until 98% of the solvent is distilled. 1700 g of water are added to the residue and the solution is purified using the method described in WO 97/30735.Yield on dry Iopamidol: 94% Contents of by-products determined with HPLC method (according to the method described in USP XXIII-NF, 1996, Vsuppl.) = 0.11% The by-product N-[2-hydroxy-1-(hydroxymethyl)ethyl]-- N'-(2,3-dihydroxypropyl)-5-(2-hydroxy-1-oxopropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide, coming from isoserinol, is under the detection limit. No presence of other by-products derived from 3-amino-1,2-propanediol are detected (see as ref. Pharmeuropa, 6, 343-345, 19949.
  • 4
  • [ 34619-03-9 ]
  • [ 534-03-2 ]
  • [ 125414-41-7 ]
YieldReaction ConditionsOperation in experiment
49% With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 1.75h; Preparation J(2-Hydroxy-1-hvdroxymethyl-ethyl)-carbamic acid tert-butyl esterO H ^OH <n="23"/>2-Amino-1 ,3-propanediol (5.Og, 54.9mmol) was dissolved in dry THF (175ml) and triethylamine (7.7ml) added. The solution was cooled in an ice-bath and di-te/f- butylcarbonate (11.98g, 54.9mmol) added in portions over 15mins. The solution was allowed to warm to ambient temperature and stirred for 90mins. The solvent was evaporated and water (250ml) added and the product extracted into ethyl acetate (4 x 125ml). The combined organics were washed with brine, dried over magnesium sulphate, filtered and evaporated. The product was isolated by recrystallization from hot ethyl acetate-petrol (1 :3) to give shiny flakes 5.18g (49% yield).The structure was confirmed by 1H NMR (300MHz , CDCI3): 1.44 (s, 9H), 3.08- 3.17 (m, 1 H), 3.61 - 3.84 (m, 4H).
  • 5
  • [ 4506-66-5 ]
  • [ 534-03-2 ]
  • N<SUP>1</SUP>,N<SUP>2</SUP>,N<SUP>4</SUP>,N<SUP>5</SUP>-tetrakis (1,3-dihydroxypropan-2-yl)-2,5-diamino-1,4-benzoquinonediimine [ No CAS ]
 

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 534-03-2 ]

Aliphatic Chain Hydrocarbons

Chemical Structure| 77-86-1

A168222 [77-86-1]

2-Amino-2-(hydroxymethyl)propane-1,3-diol

Similarity: 0.81

Chemical Structure| 1185-53-1

A104132 [1185-53-1]

2-Amino-2-(hydroxymethyl)propane-1,3-diol hydrochloride

Similarity: 0.76

Chemical Structure| 78531-29-0

A622493 [78531-29-0]

1,3-Dimethoxypropan-2-amine

Similarity: 0.76

Chemical Structure| 124-68-5

A101633 [124-68-5]

2-Amino-2-methyl-1-propanol

Similarity: 0.75

Chemical Structure| 5856-62-2

A424986 [5856-62-2]

(S)-2-Aminobutan-1-ol

Similarity: 0.71

Alcohols

Chemical Structure| 77-86-1

A168222 [77-86-1]

2-Amino-2-(hydroxymethyl)propane-1,3-diol

Similarity: 0.81

Chemical Structure| 1185-53-1

A104132 [1185-53-1]

2-Amino-2-(hydroxymethyl)propane-1,3-diol hydrochloride

Similarity: 0.76

Chemical Structure| 124-68-5

A101633 [124-68-5]

2-Amino-2-methyl-1-propanol

Similarity: 0.75

Chemical Structure| 5856-63-3

A494024 [5856-63-3]

(R)-2-Aminobutan-1-ol

Similarity: 0.71

Chemical Structure| 5856-62-2

A424986 [5856-62-2]

(S)-2-Aminobutan-1-ol

Similarity: 0.71

Amines

Chemical Structure| 77-86-1

A168222 [77-86-1]

2-Amino-2-(hydroxymethyl)propane-1,3-diol

Similarity: 0.81

Chemical Structure| 1185-53-1

A104132 [1185-53-1]

2-Amino-2-(hydroxymethyl)propane-1,3-diol hydrochloride

Similarity: 0.76

Chemical Structure| 78531-29-0

A622493 [78531-29-0]

1,3-Dimethoxypropan-2-amine

Similarity: 0.76

Chemical Structure| 124-68-5

A101633 [124-68-5]

2-Amino-2-methyl-1-propanol

Similarity: 0.75

Chemical Structure| 5856-63-3

A494024 [5856-63-3]

(R)-2-Aminobutan-1-ol

Similarity: 0.71