(S)-N-(tert-butyloxycarbonyl)-2-bromo-4,5-dihydroxyphenylalaninemethyl ester

Base Information

• Chemical Name: (S)-N-(tert-butyloxycarbonyl)-2-bromo-4,5-dihydroxyphenylalaninemethyl ester
• CAS No.: 211619-93-1
• Molecular Formula: C₁₅H₂₀BrNO₆
• Molecular Weight: 390.231
• Mol file: 211619-93-1.mol

Synonyms:(S)-N-(tert-butyloxycarbonyl)-2-bromo-4,5-dihydroxyphenylalaninemethyl ester

Chemical Property of (S)-N-(tert-butyloxycarbonyl)-2-bromo-4,5-dihydroxyphenylalaninemethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-(tert-butyloxycarbonyl)-2-bromo-4,5-dihydroxyphenylalaninemethyl ester

There total 4 articles about (S)-N-(tert-butyloxycarbonyl)-2-bromo-4,5-dihydroxyphenylalaninemethyl ester 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: 70.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-Amino-3-(2-bromo-4,5-dihydroxy-phenyl)-propionic acid methyl ester; hydrochloride → (S)-N-(tert-butyloxycarbonyl)-2-bromo-4,5-dihydroxyphenylalaninemethyl ester (211619-93-1)

Guidance literature:

With triethylamine; In methanol; for 12h;

DOI:10.1021/jo972035w

Reference yield: 69.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-Amino-3-(2-bromo-4,5-dihydroxy-phenyl)-propionic acid methyl ester (740784-70-7) → (S)-N-(tert-butyloxycarbonyl)-2-bromo-4,5-dihydroxyphenylalaninemethyl ester (211619-93-1)

Guidance literature:

With triethylamine; In methanol;

DOI:10.1016/S0040-4039(97)00494-2

Reference yield:

levodopa (59-92-7,90638-38-3) → (S)-N-(tert-butyloxycarbonyl)-2-bromo-4,5-dihydroxyphenylalaninemethyl ester (211619-93-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Br₂, 2.) SOCl₂ / 1.) acetic acid, room temp., 1.5 h, 2.) 0 deg C to room temp., 15 h

2: 70 percent / Et₃N / methanol / 12 h

With thionyl chloride; bromine; triethylamine; In methanol;

DOI:10.1021/jo972035w

upstream raw materials:

di-tert-butyl dicarbonate

(S)-2-Amino-3-(2-bromo-4,5-dihydroxy-phenyl)-propionic acid methyl ester

levodopa

(S)-2-Amino-3-(2-bromo-4,5-dihydroxy-phenyl)-propionic acid

Downstream raw materials:

C₂₅H₃₆⁽¹⁸⁾FNO₁₀

(5-fluoro)DOPA

N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-trimethylstannyl-L-phenylalaninemethyl ester

N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-bromo-L-phenylalaninemethyl ester