(S)-tert-butyl (3-chlorophenyl)(1-oxopropan-2-yl)carbamate

Base Information

• Chemical Name: (S)-tert-butyl (3-chlorophenyl)(1-oxopropan-2-yl)carbamate
• CAS No.: 1114547-48-6
• Molecular Formula: C₁₄H₁₈ClNO₃
• Molecular Weight: 283.755
• Mol file: 1114547-48-6.mol

Synonyms:(S)-tert-butyl (3-chlorophenyl)(1-oxopropan-2-yl)carbamate

Chemical Property of (S)-tert-butyl (3-chlorophenyl)(1-oxopropan-2-yl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-tert-butyl (3-chlorophenyl)(1-oxopropan-2-yl)carbamate

There total 1 articles about (S)-tert-butyl (3-chlorophenyl)(1-oxopropan-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:

3-iodochlorobenzene (625-99-0) → (S)-tert-butyl (3-chlorophenyl)(1-oxopropan-2-yl)carbamate (1114547-48-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium phosphate; copper(l) iodide / isopropyl alcohol; ethylene glycol / 24 h / 80 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 14 h / 50 °C

3.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C

3.2: 6 h / -78 - 20 °C / Inert atmosphere

3.3: 20 h / 20 °C / Inert atmosphere

4.1: oxalyl dichloride / dimethyl sulfoxide; dichloromethane / 0.33 h / -65 - -55 °C / Inert atmosphere

4.2: 0.5 h / -65 - -55 °C / Inert atmosphere

With 1H-imidazole; potassium phosphate; copper(l) iodide; n-butyllithium; oxalyl dichloride; In tetrahydrofuran; hexane; dichloromethane; ethylene glycol; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol; 1.1: |Ullmann-Goldberg Substitution / 4.1: |Swern Oxidation / 4.2: |Swern Oxidation;

DOI:10.1016/j.bmc.2017.04.018

Reference yield: 38.0%

(S)-tert-butyl (3-chlorophenyl)(1-oxopropan-2-yl)carbamate (1114547-48-6) + Ethyl bromodifluoroacetate (667-27-6) → (4S,5S)-1-(3-chlorophenyl)-3,3-difluoro-4-hydroxy-5-methylpyrrolidin-2-one (1114547-50-0) + ethyl 2-{(4S,5R)-3-(3-chlorophenyl)-4-methyl-2-oxooxazolidin-5-yl}-2,2-difluoroacetate

Guidance literature:

(S)-tert-butyl (3-chlorophenyl)(1-oxopropan-2-yl)carbamate; Ethyl bromodifluoroacetate; With zinc; In tetrahydrofuran; at 20 ℃; for 1h; Reflux; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

With diisopropylamine; In tetrahydrofuran; for 12h; Overall yield = 58 %; Overall yield = 16.2 g; Reflux; Inert atmosphere;

DOI:10.1016/j.bmc.2017.04.018

Reference yield: 21.0%

(S)-tert-butyl (3-chlorophenyl)(1-oxopropan-2-yl)carbamate (1114547-48-6) + Ethyl bromodifluoroacetate (667-27-6) → (4S,5S)-1-(3-chlorophenyl)-3,3-difluoro-4-hydroxy-5-methylpyrrolidin-2-one (1114547-50-0)

Guidance literature:

(S)-tert-butyl (3-chlorophenyl)(1-oxopropan-2-yl)carbamate; Ethyl bromodifluoroacetate; With zinc; In tetrahydrofuran; for 1h; Heating / reflux;

With hydrogenchloride; In ethyl acetate; at 20 ℃; for 2h;

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 12h; Heating / reflux;

upstream raw materials:

3-iodochlorobenzene

Downstream raw materials:

(4S,5S)-1-(3-chlorophenyl)-3,3-difluoro-4-hydroxy-5-methylpyrrolidin-2-one

2'-chloro-4'-{(2R,3S)-4,4-difluoro-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl}benzonitrile

Refernces