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[ CAS No. 183905-31-9 ]

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Chemical Structure| 183905-31-9
Chemical Structure| 183905-31-9
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Product Details of [ 183905-31-9 ]

CAS No. :183905-31-9 MDL No. :MFCD09842277
Formula : C7H12ClNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :GOJJPJCUSDMTAT-SSDOTTSWSA-N
M.W :193.63 Pubchem ID :7357675
Synonyms :

Calculated chemistry of [ 183905-31-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.71
Num. rotatable bonds : 6
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.85
TPSA : 55.4 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.73
Log Po/w (XLOGP3) : 0.09
Log Po/w (WLOGP) : 0.29
Log Po/w (MLOGP) : 0.53
Log Po/w (SILICOS-IT) : 0.88
Consensus Log Po/w : 0.71

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.7
Solubility : 38.5 mg/ml ; 0.199 mol/l
Class : Very soluble
Log S (Ali) : -0.81
Solubility : 30.1 mg/ml ; 0.156 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.82
Solubility : 2.92 mg/ml ; 0.0151 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.45

Safety of [ 183905-31-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 183905-31-9 ]

* 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.

  • Upstream synthesis route of [ 183905-31-9 ]
  • Downstream synthetic route of [ 183905-31-9 ]

[ 183905-31-9 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 183905-31-9 ]
  • [ 154590-66-6 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 44, p. 7937 - 7940
  • 2
  • [ 108-24-7 ]
  • [ 183905-31-9 ]
YieldReaction ConditionsOperation in experiment
89% With pyridine In dichloromethane at 20 - 40℃; for 22 h; Acetic anhydride (4.70 mL, 49.70 mmol) was added to a slurry of (2S)-1-amino-3-chloro-2-propanol hydrochloride (3.50 g, 21.60 mmol) in dichloromethane (8 mL). The slurry was warmed to 38° C., and pyridine (2.2 mL, 27.22 mmol) was added while maintaining temperature at 36-40° C. The resulting solution was stirred at the same temperature for 5 hours and then at ambient temperature for 17 hours. The reaction was quenched at 0-5° C. with water (10 mL) and aqueous potassium carbonate (6 g, 12 mL water), and extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated. The resulting residue was then taken into toluene (2.x.10 mL), and the mixture was concentrated after each addition. Hexane (20 mL) was added to the resulting milky residue and the slurry was stirred at 0-5° C. for 20 minutes. The precipitate was collected by vacuum filtration, washed with hexanes and dried under reduced pressure to give the title compound. Yield: 3.71 g (89percent). 1H-NMR (CDCl3) δ: 1.98 (s, 3H), 2.09 (s, 3H), 3.42-3.66 (m, 3H), 3.67 (dd, 1H, J=12.0, 4.8 Hz), 5.07 (m, 1H), 6.10 (br s, 1H).
75% With pyridine In dichloromethane at 18 - 40℃; for 5 h; A stirred solution of dichloromethane (220.8 ml) containing the step-I salt (96 g, 0.66 mol) was cooled to 18-20°C. Acetic anhydride (154.78 g, 1.5175 mol) was added slowly (slight exothermic). Pyridine (67.76 g, 0.8577 mol) was added slowly (exothermic) while maintaining the temperature at 18-20°C. The resulting mixture was heated to 40°C for 5 hours. The reaction mixture was allowed to cool to room temperature and stirring continued for further 16 hours. The reaction mass was cooled to 3-6°C and diluted with 170 ml of fresh water. To this was added an aqueous solution of potassium carbonate (191.2 g of K2C03 in 382 ml water). The reaction mixture was further diluted with additional dichloromethane (170 ml) and water (425 ml). The reaction mass was stined well and the dichloromethane layer separated. The aqueous layer was further extracted with 2x170 ml dichloromethane. The combined dichloromethane layer was washed with aqueous sodium chloride solution (13.6 g of sodium chloride in 493 ml water). The solvent was evaporated till a volume of 170 ml and the residual layer was diluted with toluene (340 ml), stined well and the solvent was evaporated completely at 40°C under reduced pressure (4 mm Hg). To the residue ethyl acetate (170 ml) and hexane (187 ml) were added and the mixture stirred for 30 minute. The separated solid was filtered under suction and the residue washed with 50 ml of a 1:1 mixture of ethyl acetate and hexane. The solid obtained was dried under reduced pressure (4 mm Hg) at 45°C for 3.5 hours, to obtain 96 g of acetic acid 1-(acetylamino-methyl)-2-chloro-ethyl ester (III) as a white solid, in 75percent yield.Analysis:Mass: 194 (M+1); for Molecular Weight: 193 and Molecular Formula: C7H12C1NO31H NMR (400 MHz, CDC13): 5 5.69 (s, 1H), 5.0-5.1 (m, 1H), 3.4-3.7 (m, 4H), 2.1 (s,3H), 1.9 (s, 3H).
47.98% at 20℃; 53.6 g (281 mmol) of (S)-1-amino-3-chloro-2-propanol hydrochloride was dissolved in 165 mL (2050mmol) of pyridine to form a solution. Then, 106 mL (1123 mmol) acetic anhydride (Ac2O) was added dropwise into thesolution at room temperature over 90 minutes, and the resultant mixture was stirred overnight. After rotary evaporationof the solvent, the pH of the residue was adjusted to be acidic with diluted hydrochloric acid, and then extracted threetimes with dichloromethane. The dichloromethane in the combined organic layer was removed by rotary evaporation toafford a crude product, which was recrystallized with a mixed solution of ethyl acetate and n-heptane (1:3) to obtain 50.2g white crystal. The total yield of the two steps of reaction is 47.98percent.[0067] 1H-NMR (400 MHz, CDCl3): δ 5.78 (br, s, 1H), 5.11-5.08(m, 1H), 3.69(dd, J = 12Hz, J = 4.4Hz, 1H), 3.67-3.57(m,2H), 3.55-3.48(m, 1H).[0068] ESI-MS m/z (M+H+): 194.14.
50.2 g at 20℃; To 42.26 mL (540 mmol) (S)-epoxy chloropropane, 250 mL ethanol, 57 mL aqueous ammonia, and 56.5 mL benzaldehyde were added in sequence with stirring, upon which a white solid precipitated and then disappeared soon. The mixture was stirred for further 20 hours at room temperature, followed by rotary evaporation. Then, 81.7 mL concentrated hydrochloric acid was added to the residue, and the resultant mixture was stirred for 2 hours at room temperature, followed by rotary evaporation of the solvent. The solid obtained was recrystallized with ethanol. After chilling in a refrigerator overnight, filtration was performed to afford 53.6 g of (S)-1-amino-3-chloro-2-propanol hydrochloride as white powder. 53.6 g (281 mmol) of (S)-1-amino-3-chloro-2-propanol hydrochloride was dissolved in 165 mL (2050 mmol) of pyridine to form a solution. Then, 106 mL (1123 mmol) acetic anhydride (Ac2O) was added dropwise into the solution at room temperature over 90 minutes, and the resultant mixture was stirred overnight. After rotary evaporation of the solvent, the pH of the residue was adjusted to be acidic with diluted hydrochloric acid, and then extracted three times with dichloromethane. The dichloromethane in the combined organic layer was removed by rotary evaporation to afford a crude product, which was recrystallized with a mixed solution of ethyl acetate and n-heptane (1:3) to obtain 50.2 g white crystal. The total yield of the two steps of reaction is 47.98percent. [0181] 1H-NMR (400 MHz, CDCl3): δ 5.78 (br, s, 1H), 5.11-5.08 (m, 1H), 3.69 (dd, J=12 Hz, J=4.4 Hz, 1H), 3.67-3.57 (m, 2H), 3.55-3.48 (m, 1H). [0182] ESI-MS m/z (M+H+): 194.14.

Reference: [1] Patent: US2008/146573, 2008, A1, . Location in patent: Page/Page column 27
[2] Patent: WO2015/173664, 2015, A1, . Location in patent: Paragraph 10
[3] Patent: EP2738169, 2014, A1, . Location in patent: Paragraph 0065; 0066; 0067; 0068
[4] Patent: US6362334, 2002, B1, . Location in patent: Example 14
[5] Patent: US2014/142144, 2014, A1, . Location in patent: Paragraph 0179; 0180; 0181; 0182
[6] Patent: WO2017/66964, 2017, A1, . Location in patent: Page/Page column 46; 47
  • 3
  • [ 75-36-5 ]
  • [ 183905-31-9 ]
YieldReaction ConditionsOperation in experiment
86.1% With pyridine In dichloromethane at 0 - 20℃; for 10 h; To the reaction flask, 50.0 g (342 mmol) of the formula (2), CH2Cl2 200 mL, and 34.0 g (431 mmol) of pyridine, 70.6 g (900 mmol) of acetyl chloride was added dropwise at 0 to 10 °C, and the mixture was added dropwise and reacted at room temperature for 10 hours. 10 °C, 600 mL of an aqueous solution containing 95.0 g of sodium bicarbonate was added slowly, the organic layer was separated, the aqueous layer was extracted with CH2Cl2, the organic layers were combined. Saturated salt water washing, evaporated solvent, the amount of toluene azeotropic water twice, oil ether crystallization, ethyl acetate - petroleum ether refining, drying, afforded 57 g of a white solid, yield 86.1percent.
Reference: [1] Patent: CN103864773, 2017, B, . Location in patent: Paragraph 0074; 0082; 0083
  • 4
  • [ 108-24-7 ]
  • [ 183905-31-9 ]
YieldReaction ConditionsOperation in experiment
90.6% With pyridine In dichloromethane at 30℃; for 20 h; In the reaction flask, (S)-1-amino-3-chloro-2-propanol hydrochloride (50.0 g, 342 mmol), dichloromethane (200 mL), acetic anhydride (80.0 g, 786 mmol), and 34.0 g (431 mmol) of pyridine was added thereto at 30 ° C. After completion of the drop, the incubation reaction was carried out for 20 h. 6 ° C, 500 mL of an aqueous solution containing 90.0 g of sodium bicarbonate was slowly added, and the organic layer was separated,The aqueous layer was extracted with CH2Cl2, the combined organic layers were washed with saturated brine, evaporated to dry the solvent, the amount of toluene azeotrope with water twice, petroleum ether crystallization, ethyl acetate - petroleum ether refining, drying, the white solid 60g, the yield of 90.6percent.
Reference: [1] Patent: CN103864773, 2017, B, . Location in patent: Paragraph 0074; 0080; 0081
  • 5
  • [ 108-24-7 ]
  • [ 53494-57-8 ]
  • [ 183905-31-9 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 44, p. 7937 - 7940
  • 6
  • [ 108-24-7 ]
  • [ 183905-31-9 ]
Reference: [1] Organic Process Research and Development, 2003, vol. 7, # 4, p. 533 - 546
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