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[ CAS No. 107017-73-2 ] {[proInfo.proName]}

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Chemical Structure| 107017-73-2
Chemical Structure| 107017-73-2
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Quality Control of [ 107017-73-2 ]

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Product Details of [ 107017-73-2 ]

CAS No. :107017-73-2 MDL No. :MFCD09749954
Formula : C9H17NO3 Boiling Point : No data available
Linear Structure Formula :- InChI Key :HFMAZNJKNNRONT-UHFFFAOYSA-N
M.W : 187.24 Pubchem ID :11286907
Synonyms :

Calculated chemistry of [ 107017-73-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.89
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 48.98
TPSA : 58.56 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 0.62
Log Po/w (WLOGP) : 0.97
Log Po/w (MLOGP) : 0.56
Log Po/w (SILICOS-IT) : 0.78
Consensus Log Po/w : 0.97

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.06
Solubility : 16.3 mg/ml ; 0.0868 mol/l
Class : Very soluble
Log S (Ali) : -1.42
Solubility : 7.05 mg/ml ; 0.0376 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.48
Solubility : 6.19 mg/ml ; 0.033 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.15

Safety of [ 107017-73-2 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338-P310 UN#:
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 107017-73-2 ]

* 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 [ 107017-73-2 ]

[ 107017-73-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 107017-73-2 ]
  • [ 107259-06-3 ]
YieldReaction ConditionsOperation in experiment
99% With oxalyl dichloride; triethylamine; In dichloromethane; dimethyl sulfoxide; at -78℃; for 1h; To a solution of oxalyl dichloride (277 mg, 2.2 mmol) in DCM (5 mL) was added DMSO (1 mL) and NEt3 (333 mg, 3.3 mmol). The resulting solution was stirred at -78C for lh. Then a solution of compound 2 (200 mg, 1.1 mmol) in 2 mL DCM was added. The reaction was stirred at -78 C for 1 h. Quenched by NH4C1 aq. and extracted by ethyl acetate. Organic layer was combined, dried over Na2SO4 and concentrated to give tert-butyl 1 -formylcyclopropylcarbamate (196 mg, 99%).
90% With 4-methylmorpholine N-oxide;tetrapropylammonium perruthennate; In dichloromethane; at 0 - 20℃; for 1h; [0505] To a suspension of 1-aminocyclopropanecarboxylic acid (998 mg, 9.87 mmol) in EtOH (25 mL), cooled to 0 C., was added SOCl2 (2.0 mL, 27 mmol) dropwise over 10 minutes. The resulting solution was heated at reflux under nitrogen for 2 hours, then was evaporated under reduced pressure, giving the ester as a light brown oil. [0506] This material was dissolved into EtOAc (25 mL) and a solution of KHCO3 (1.51 g, 15.1 mmol) in H2O (9 mL) was added dropwise. The resulting solution was cooled to 0 C. and a solution of Boc2O (2.97 g, 13.6 mmol) in EtOAc (10 mL) was added. The reaction was stirred at room temperature for 16 hours, the layers were separated and the aqueous solution was extracted with EtOAc (25 mL). The combined organic solution was dried (MgSO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (EtOAc/hexane, 1:3) gave the protected amine as light brown solid (1.27 g, 5.54 mmol, 56%). 1H NMR (CDCl3) δ 1.08-1.18 (m, 2H), 1.23 (t, 3H, J=7.2 Hz), 1.44 (s, 9H), 1.46-1.53 (m, 2H), 4.14 (q, 2H, J=7.2 Hz), 5.13 (br. s, 1H). [0507] Preparation of (1-hydroxymethyl-cyclopropyl)-carbamic Acid Tert-Butyl Ester: [0508] To a solution of the ester (1.18 g, 5.15 mL) in THF (10 mL) under nitrogen was added a solution of LiBH4 (200 mg, 9.2 mmol) in THF (10 mL) dropwise over 10 minutes. The reaction was stirred at room temperature for 17.5 hours, then was cooled to 0 C. A solution of 50% HOAc was added dropwise until the evolution of gas had ceased (approx. 8 mL). The resulting white suspension was diluted with H2O (15 mL) and was extracted with Et2O (30 mL). The organic solution was washed with 15% aqueous NaHCO3 (15 mL) and brine (15 mL), then dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (EtOAc/hexane, 1:1) gave the alcohol as a white solid (592 mg, 3.16 mmol, 61%).2 1H NMR (CDCl3) δ 0.81 (s, 4H), 1.43 (s, 9H), 3.52 (br. s, 1H), 3.58 (s, 2H), 5.12 (br. s, 1H). [0509] Preparation of (1-formyl-cyclopropyl)-carbamic Acid Tert-Butyl Ester: [0510] To a solution of the alcohol (389 mg, 2.08 mmol) in CH2Cl2 (11 mL), cooled to 0 C., was added crushed, dried 3 molecular sieves (1.05 g), NMO (382 mg, 3.26 mmol) and TPAP (76 mg, 0.22 mmol). The black mixture was stirred at 0 C. for 30 minutes and at room temperature for a further 30 minutes. The mixture was diluted with EtOAc (20 mL) and flushed through a short silica column, rinsing with EtOAc. The product containing material was concentrated under reduced pressure giving the aldehyde as a white solid (345 mg, 1.86 mmol, 90%). 1H NMR (CDCl3) δ 1.27-1.37 (m, 2H), 1.40-1.52 (m, 2H), 1.46 (s, 9H), 5.22 (br. s, 1H), 9.16 (s, 1H). [0511] Preparation of (E)-3-(i-tert-butoxycarbonylamino-cyclopropyl)-acrylic Acid Ethyl Ester: [0512] Triethyl phosphonoacetate (0.62 mL, 3.13 mmol) was added dropwise to a suspension of 60% NaH in mineral oil (120 mg, 3.00 mmol) in THF (5 mL). The resulting solution was stirred at room temperature for 10 minutes, then cooled to 0 C. for the dropwise addition of a solution of the aldehyde (463 mg, 2.50 mmol) in THF (5 mL). The reaction was stirred at 0 C. for 15 minutes, then heated to reflux for 1 hour. Once cooled to room temperature, saturated aqueous NH4Cl (10 mL) was added, the layers were separated and the aqueous solution was extracted with CH2Cl2 (10 mL×2). The organic solution was dried (MgSO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (EtOAc/hexane, 1:1) gave the unsaturated ester as a pale yellow solid (539 mg, 2.11 mmol, 84%). 1H NMR (CDCl3) δ 1.11-1.18 (m, 2H), 1.24-1.29 (m, 5H), 1.44 (s, 9H), 4.17 (q, 2H, J=7.1 Hz), 5.02 (br. s, 1H), 5.84 (d, 1H, J=15.3 Hz), 6.47 (d, 1H, J=15.6 Hz). [0513] Preparation of 3-(1-tert-butoxycarbonylamino-cyclopropyl)-propionic Acid Ethyl Ester: [0514] A solution of the unsaturated ester (495 mg, 1.94 mmol) in EtOAc (10 mL) was hydrogenated (H2 balloon) over 10% Pd/C (25 mg, 0.023 mmol) at room temperature for 3 hours. The mixture was suction filtered through Celite, washing with EtOAc and evaporation of the filtrate under reduced pressure gave the saturated ester as a colourless oil (500 mg, 1.94 mmol, 100%). 1H NMR (CDCl3) δ 0.61-0.65 (m, 1H), 0.73-0.78 (m, 1H), 0.91 (t, 2H, J=7.4 Hz), 1.25 (td, 3H, J=7.1, 1.4 Hz), 1.43 (s, 9H), 1.78-1.90 (m, 2H), 2.36 (t, 1H, J=7.7 Hz), 2.44 (t, 1H, J=7.5 Hz), 4.12 (q, 2H, J=7.1 Hz). [0515] Preparation of [1-(3-hydroxy-propyl)-cyclopropyl]-carbamic Acid Tert-Butyl Ester: [0516] LiBH4 (70 mg, 3.2 mmol) was added to a solution of the ester (500 mg, 1.94 mmol) in THF (8 mL). The reaction was stirred at room temperature under nitrogen for 18 hours, then was quenched by the dropwise addition of 50% aqueous HOAc until the evolution of gas had ceased (approx. 2 mL). The suspension was diluted with H2O (10 mL) and extracted with Et2O (15 mL). The organic solution was washed with saturated aq...
89% With sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; at -20 - -5℃; for 3.75h; To a solution of tert-butyl (1 -(hydroxymethyl)cyclopropyl)carbamate (commercial, 15 g; 80.3 mmol) in DCM (235 mL), cooled to -20C, was slowly added DIPEA (45 mL;263 mmol). A solution of Pyr.S03 (38.75 g; 110 mmol) in DMSO (108 mL, 1.5 mol) was added dropwise over 45 mm, keeping the IT below -5C. The reaction mixture was stirred at this temperature for 3 h. The reaction mixture was partitioned between water (1 L) and DCM (200 mL). The two layers were separated and the aq. layer was extracted once more with DCM (300 mL). The evaporation residue was evaporated further with toluene(2 x 300 mL) and purified by CC (Hept-EA) to afford the title product (13.18 g, 89% yield) as a white solid.‘H NMR (d6-DMSO) ?: 8.99 (s, 1H); 7.56 (s, 1H); 1.41-1.34 (overlapped m, 2H); 1.39 (s, 9H); 1.16-1.13 (m, 2H).
89% To a solution of tert-butyl (l-(hydroxymethyl)cyclopropyl)carbamate (commercial, 15 g; 80.3 mmol) in DCM (235 mL), cooled to -20C, was slowly added DIPEA (45 mL; 263 mmol) over 15min. A solution of Pyr.S03 (38.75 g; 110 mmol ) in DMSO (108 mL; 1.52 mol) was added dropwise over 45min. The reaction mixture was stirred at 0C for 2h45. The reaction mixture was partitioned between water (1 L) and DCM (200 mL). The two layers were separated and the aq. layer was extracted once more with DCM (300 mL). The evaporation residue was purified by CC (Hept-EA) to afford the title compound (13.18 g; 89% yield) as a white solid. 1H NMR (d6-DMSO) δ: 8.99 (s, 1H); 7.55 (s, 1H); 1.44-1.31 (overlapped m, 2H); 1.39 (s, 9H); 1.19-1.10 (m, 2H). MS (ESI, m/z): 186.2 [M+H+] for C9H15N03; tR = 0.62 min
87% With Dess-Martin periodane; In dichloromethane; for 1h; To a solution of tert-butyl ( 1 -(hydroxymethyl)cydopropyl)carbamate (Bioorg. Med. Chem. Lett., 2008, 18(6), 2388) (135 mg, 0.72 mmoles) in DCM (8 mL) was added Dess- Martin periodinane (277 mg, 0.65 mmole). After stirring 1 hr, the reaction was filtered through ceiite and concentrated to a yellow oil which was further purified by isolera (7%~ 70% ethyl acetate hexanes) to provide 84 mg (87 %) of tert-butyl (1-forrnylcyclopropyl)- carbamate as a white solid.
87% With Dess-Martin periodane; In dichloromethane; for 1h; To a solution of tert-butyl (1-(hydroxyrnethyl)cyclopropyl)carbamate (Bioorg. Med. Chem. Left., 2008, 18(6), 2188) (135 mg, 0.72 mmoles) in DCM (8 rnL) was added Dess Martin periodinane (277 mg, 0.65 mmole). After stiuing I hr, the reaction was filtered through celite and concentrated to a yellow oil which was further purified by Isolera (7%- 70% ethyl acetate/hexanes) to provide 84 mg (87 %) of tert-butyl (1-formylcyclopropyl)carbamate as a white solid.
87% With Dess-Martin periodane; In dichloromethane; for 1h; Step 1. To a solution of tert-butyl (1-(hydroxymethyl)cyclopropyl)carbamate (Bioorg. Med. Chem. Lett., 2008, 18(6), 2188) (135 mg, 0.72 mmoles) in DCM (8 mL) was added Dess Martin periodinane (277 mg, 0.65 mmole). After stirring 1 hr, the reaction was filtered through celite and concentrated to a yellow oil which was further purified by Isolera (7%-70% ethyl acetate/hexanes) to provide 84 mg (87 %) of tert-butyl (1-formylcyclopropyl)carbamate as a white solid.
87% With Dess-Martin periodane; In dichloromethane; for 1h; Step 1 To a solution of tert-butyl (1-(hydroxymethyl)cyclopropyl)carbamate (Bioorg. Med. Chem. Lett., 2008, 18(6), 2188) (135 mg, 0.72 mmoles) in DCM (8 mL) was added Dess-Martin periodinane (277 mg, 0.65 mmole). After stirring 1 hr, the reaction was filtered through celite and concentrated to a yellow oil which was further purified by Isolera (7%-70% ethyl acetate/hexanes) to provide 84 mg (87%) of tert-butyl (l-formylcyclopropyl)-carbamate as a white solid.
70% To a solution of oxalyl chloride (2.01 mL, 23.1 mmol) in CH2Cl2 (50 mL) at -55 C was added dropwise a solution of DMSO (1.64 mL, 23.1 mmol) in CH2Cl2 (10 mL). Upon complete addition, the reaction was stirred for 5 min then the Boc-protected amino alcohol (3.6 g, 19.2 mmol) was added as a solution in CH2Cl2 (10 mL) and stirring was continued for 15 min. Triethylamine (13.9 mL, 99.9 mmol) was added and the reaction <n="127"/>was stirred for 5 min then allowed to slowly warm to room temperature. After Ih, H2O (50 mL) was added and the reaction was poured into CH2Cl2. The aqueous phase was separated and extracted two more times with CH2Cl2. The organic layers were combined and washed with brine, dried (Na2SO4), decanted and concentrated. The resultant residue was purified via SiO2 flash chromatography (10-40% EtOAc-Hexanes) to afford Boc-1- aminocyclopropane-1-carboxaldehyde as a white solid (2.5g, 70%).
60% A solution of DMSO (0.391 mL, 5.51 mmol) in DCM (2.4 mL) was added dropwise to a solution of oxalyl chloride (0.482 mL, 5.51 mmol) in DCM (12 mL) at -70 C with stirring under nitrogen. The mixture was stirred for 5 mm, then a solution of 5A (0.860 g, 4.59 mmol) in DCM (2.4 mL) was addeddropwise. The mixture was stirred at -70 C for 15 mm, and then TEA (3.20 mL,23.0 mmol) was added. After an additional 5 mm at -70 C, the cooling bath was removed, and the reaction mixture was allowed to slowly warm to rt. Stirring was continued for 1 h. The reaction was quenched with water and poured into DCM. The phases were separated, and the aq. layer was extracted with DCM(2x). The combined extracts were washed with brine, dried over Na2504 and filtered. The filtrate was evaporated, and the residue was purified by flash chromatography to provide SB as a white crystalline solid (0.5 13 g, 60 %) was obtained. MS (ESI) m/z 186.4 (M+H).
With sodium hypochlorite; TEMPOL; sodium hydrogencarbonate; In dichloromethane; water; at 0 - 25℃; for 1h; Three 500mL flask was added compound 1A (7g, 0.037mol, 1eq) and dichloromethane (50mL), addThe 4-OH-TEMPO (0.06g, 0.37mmol, 0.01eq), was added saturated aqueous NaHCO3 (200mL),Cooled to 0 deg.] C, was added dropwise an aqueous solution of 10% NaClO (50g, 0.067mol, 1.8eq), naturally warmed to room temperature,The reaction 1h. Water was added 100mL, extracted with dichloromethane (150mL * 2), the combined organic phases were washed with water (200 mL)Washed once, the organic phase was concentrated to give compound 2A as a pale yellow solid (6.3 g of, yield: 91%, purity:94.2%)

  • 2
  • [ 107017-73-2 ]
  • [ 115652-52-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In 1,4-dioxane; at 20℃; 8.2 1-aminocyclopropanemethanol 1.04 g tert-butyl (1-hydroxymethylcyclopropyl)-carbamidate are placed in 5 ml dioxane. 2.5 ml HCl in dioxane (4 mol/l) are added dropwise. The reaction mixture is stirred for 15 h at ambient temperature. The solvent is evaporated down by half and the precipitated solid is suction filtered. 0.5 g product are obtained as the hydrochloride. 1H NMR (400 MHz, DMSO): 5.27 (1H, t); 0.91 (2H, t); 0.71 (2H, t).
With hydrogenchloride; In 1,4-dioxane; at 20℃; for 0.25h; 2.2 1-aminocyclopropanemethanol 1.04 g tert-butyl (1-hydroxymethylcyclopropyl)-carbamidate are placed in 5 ml dioxane. 2.5 ml HCl in dioxane (4 mol/l) are added dropwise. The reaction mixture is stirred for 15 h at ambient temperature. The solvent is evaporated down by half and the precipitated solid is suction filtered. 0.5 g product are obtained as the hydrochloride. 1H NMR (400 MHz, DMSO): 5.27 (1H, t); 0.91 (2H, t); 0.71 (2H, t).
With hydrogenchloride; In 1,4-dioxane; at 20℃; 1.3.2 1-aminocyclopropanemethanol 1.04 g tert-butyl (1-hydroxymethylcyclopropyl)-carbamidate are placed in 5 ml dioxane. 2.5 ml HCl in dioxane (4 mol/l) are added dropwise. The reaction mixture is stirred for 15 h at ambient temperature. The solvent is evaporated down by half and the precipitated solid is suction filtered. 0.5 g product are obtained as the hydrochloride. 1H NMR (400 MHz, DMSO): 5.27 (1H, t); 0.91 (2H, t); 0.71 (2H, t).
With hydrogenchloride; In 1,4-dioxane; at 20℃; for 15h; 4.2 1-aminocyclopropanemethanol1.04 g tert-butyl (1-hydroxymethylcyclopropyl)-carbamidate are placed in 5 ml dioxane. 2.5 ml HCl in dioxane (4 mol/l) are added dropwise. The reaction mixture is stirred for 15 h at ambient temperature. The solvent is evaporated down by half and the precipitated solid is suction filtered. 0.5 g product are obtained as the hydrochloride.1H NMR (400 MHz, DMSO): 5.27 (1H, t); 0.91 (2H, t); 0.71 (2H, t).
0.5 g With hydrogenchloride; In 1,4-dioxane; at 20℃; for 15h; 8.2 1-aminocyclopropanemethanol 1.04 g tert-butyl (1-hydroxymethylcyclopropyl)-carbamidate are placed in 5 ml dioxane. 2.5 ml of HCl in dioxane (4 mol/l) are added dropwise. The reaction mixture is stirred for 15 h at ambient temperature. The solvent is evaporated down by half and the precipitated solid is suction filtered. 0.5 g product are obtained as the hydrochloride. 1H NMR (400 MHz, DMSO): 5.27 (1H, t); 0.91 (2H, t); 0.71 (2H, t).

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