tert-Butyl ((2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

Base Information

• Chemical Name: tert-Butyl ((2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
• CAS No.: 162536-40-5
• Molecular Formula: C15H22ClNO3
• Molecular Weight: 299.798
• European Community (EC) Number: 923-366-1
• DSSTox Substance ID: DTXSID30433180
• Nikkaji Number: J882.856C
• Wikidata: Q72509719
• Mol file: 162536-40-5.mol

Synonyms:162536-40-5;tert-Butyl ((2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate;tert-butyl N-[(2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]carbamate;(2R,3S)-3-(TERT-BUTOXYCARBONYLAMINO)-1-CHLORO-2-HYDROXY-4-PHENYLBUTANE;tert-Butyl [(2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]carbamate;tert-butyl n-((2s,3r)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate;MFCD01317802;Carbamic acid, N-[(1S,2R)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl]-, 1,1-dimethylethyl ester;SCHEMBL640670;AMY4338;DTXSID30433180;AKOS015911527;AC-8238;Carbamicacid, N-[(1S,2R)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl]-, 1,1-dimethylethylester;DS-16364;CS-0000118;C73120;A882833;(2R,3S)-1-Chloro-3-(tert-butoxycarbonylamino)-4-phenyl-2-butanol;(2R,3S)-1-chloro-3-tert-butoxycarbonylamino-4-phenyl-2-butanol;(2R, 3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane;(2R, 3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4phenylbutane;(2r,3s)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane;(2r,3s)-N-t-butoxycarbonyl-3-amino-1-chloro-2-hydroxy-4-phenylbutane;tert-Butyl((2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate;Carbamicacid,N-[(1S,2R)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl]-,1,1-dimethylethylester;Carbamic acid,N-[(1S,2R)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl]-,1,1-dimethylethyl ester

Chemical Property of tert-Butyl ((2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 83-84℃
• Refractive Index: 1.527
• Boiling Point: 460.456 °C at 760 mmHg
• PKA: 11.92±0.46(Predicted)
• Flash Point: 232.276 °C
• PSA: 58.56000
• Density: 1.154 g/cm³
• LogP: 3.11300
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 299.1288213
• Heavy Atom Count: 20
• Complexity: 298

Purity/Quality:

99% ^*data from raw suppliers

tert-Butyl((2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1)C(CCl)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](CCl)O

Technology Process of tert-Butyl ((2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

There total 20 articles about tert-Butyl ((2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.6%

→ (2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane (162536-40-5)

Guidance literature:

Reference yield: 98.7%

(2R,3S)-1-chloro-3-amino-4-phenyl-2-butanol sulfuric acid salt (934971-02-5) + di-tert-butyl dicarbonate (24424-99-5) → (2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane (162536-40-5)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 2h; under 760.051 Torr; Time;

Reference yield: 97.0%

(S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate (102123-74-0) → (2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane (162536-40-5)

Guidance literature:

With Rhodococcus erythropolis SC 13845; In phosphate buffer; for 49h; pH=7.0; Microbiological reaction;

DOI:10.1016/j.tetasy.2003.07.016

upstream raw materials:

(S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

N-tert-butoxycarbonyl-L-phenylalanine

(3S)-tert-butyl 1-benzyl-3-diazo-2-oxopropylcarbamate

Downstream raw materials:

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

(2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol hydrochloride

atazanavir sulphate

atazanavir

Refernces

• 1、 Patel, Ramesh N.,Chu, Linda,Mueller, Richard. "Diastereoselective microbial reduction of (S)-[3-chloro-2-oxo-1- (phenylmethyl)propyl]carbamic acid, 1,1-dimethylethyl ester". . p. 3105 - 3109. Retrieved 2003.
• 2、 -. "Synthetic method of HIV protease inhibitor intermediate compound". Paragraph 0032-0050; 0053-0056. . Retrieved 2021/03/06.
• 3、 -. "A (2 R, 3 S) - 1 - chloro - 3 - tert-butoxy amide - 4 - phenyl - 2 - butanol preparation method". Paragraph 0035; 0038; 0053; 0054; 0088. . Retrieved 2017/09/26.