N-(t-Butoxycarbonyl)-3-(4-nitrobenzyl)-L-histidine methyl ester

Base Information

• Chemical Name: N-(t-Butoxycarbonyl)-3-(4-nitrobenzyl)-L-histidine methyl ester
• CAS No.: 111102-61-5
• Molecular Formula: C₁₉H₂₄N₄O₆
• Molecular Weight: 404.423
• Mol file: 111102-61-5.mol

Synonyms:N-(t-Butoxycarbonyl)-3-(4-nitrobenzyl)-L-histidine methyl ester

Chemical Property of N-(t-Butoxycarbonyl)-3-(4-nitrobenzyl)-L-histidine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(t-Butoxycarbonyl)-3-(4-nitrobenzyl)-L-histidine methyl ester

There total 7 articles about N-(t-Butoxycarbonyl)-3-(4-nitrobenzyl)-L-histidine methyl 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:

(4-nitrophenyl)methyl trifluoromethanesulfonate (114533-06-1) + 4-(2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-1H-imidazole-1-carboxylic acid tert-butyl ester (20898-43-5,133467-03-5,165062-56-6) → N-(t-Butoxycarbonyl)-3-(4-nitrobenzyl)-L-histidine methyl ester (111102-61-5)

Guidance literature:

Yield given. Multistep reaction; 1.) CH₂Cl₂, from -75 deg C to RT, 8 h, 2.) CH₂Cl₂, pH 7, 1.5 h;

DOI:10.1021/jm00115a014

Reference yield:

5-(2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-1-(4-nitro-benzyl)-3-trityl-3H-imidazol-1-ium; bromide → N-(t-Butoxycarbonyl)-3-(4-nitrobenzyl)-L-histidine methyl ester (111102-61-5)

Guidance literature:

With silica gel; trifluoroacetic acid; In methanol; dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/S0040-4039(00)01792-5

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N-(t-Butoxycarbonyl)-3-(4-nitrobenzyl)-L-histidine methyl ester (111102-61-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / methanol; triethylamine / 24 h

2: CH₂Cl₂ / -78 °C

In methanol; dichloromethane; triethylamine;

DOI:10.1021/ja0277226

upstream raw materials:

(4-nitrophenyl)methyl trifluoromethanesulfonate

4-(2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-1H-imidazole-1-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

l-histidine methyl ester dihydrochloride

Downstream raw materials:

3-(4-Nitrobenzyl)-L-histidine dihydrochloride

(S)-1-(4-Nitro-benzyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester

(S)-(-)-1-[(4-aminophenyl)-methyl]-5-(diphenylacetyl)-4,5,6,7-tetrahydro-1H-imidazo-[4,5-c]pyridine-6-carboxylic acid

(S)-1-(4-Amino-benzyl)-5-diphenylacetyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester