Carbamic acid, [2-(1H-imidazol-1-yl)-2-oxo-1-(phenylmethyl)ethyl]-, 1,1-dimethylethyl ester, (S)-

Base Information

• Chemical Name: Carbamic acid, [2-(1H-imidazol-1-yl)-2-oxo-1-(phenylmethyl)ethyl]-, 1,1-dimethylethyl ester, (S)-
• CAS No.: 34101-07-0
• Molecular Formula: C17H21N3O3
• Molecular Weight: 315.372
• Mol file: 34101-07-0.mol

Synonyms:N-(tert-butoxycarbonyl)-L-phenylalanylimidazole;(S)-tert-butyl 1-(1H-imidazol-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate;t-butyloxycarbonyl-L-phenylalanylimidazole;

Chemical Property of Carbamic acid, [2-(1H-imidazol-1-yl)-2-oxo-1-(phenylmethyl)ethyl]-, 1,1-dimethylethyl ester, (S)-

Chemical Property:

• PSA: 73.22000
• LogP: 3.05020

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Carbamic acid, [2-(1H-imidazol-1-yl)-2-oxo-1-(phenylmethyl)ethyl]-, 1,1-dimethylethyl ester, (S)-

There total 3 articles about Carbamic acid, [2-(1H-imidazol-1-yl)-2-oxo-1-(phenylmethyl)ethyl]-, 1,1-dimethylethyl ester, (S)- 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: 97.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + 1,1'-carbonyldiimidazole (530-62-1) → (2S)-2-[N-(tert-butoxycarbonyl)amino]-1-imidazol-1-yl-3-phenylpropan-1-one (34101-07-0)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/jo982501x

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + 1,1'-carbonyldiimidazole (530-62-1) → C18H21N3O5 (1247065-59-3) + (2S)-2-[N-(tert-butoxycarbonyl)amino]-1-imidazol-1-yl-3-phenylpropan-1-one (34101-07-0)

Guidance literature:

In tetrahydrofuran; at 45 ℃; for 72h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2S)-2-[N-(tert-butoxycarbonyl)amino]-1-imidazol-1-yl-3-phenylpropan-1-one (34101-07-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide; tetrabutylammomium bromide / water / 0.08 h / 25 - 30 °C

1.2: 16 h / 0 - 30 °C

2.1: dichloromethane / 1 h / -7 - -3 °C / Inert atmosphere

With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; water;

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

1,1'-carbonyldiimidazole

di-tert-butyl dicarbonate

Downstream raw materials:

(S)-3-tert-butoxycarbonylamino-1-nitro-4-phenyl-2-butanone

(3R)-3-tert-butoxycarbonylamino-1-nitro-2-oxo-4-phenylbutane

Boc-L-phenylalaninal

(S)-tert-butyl 1-(7-hydroxy-2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)-2-phenylethyl carbamate