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

Base Information

• Chemical Name: N-(t-Butoxycarbonyl)-3-(4-methoxybenzyl)-L-histidine methyl ester
• CAS No.: 111102-62-6
• Molecular Formula: C₂₀H₂₇N₃O₅
• Molecular Weight: 389.451
• Mol file: 111102-62-6.mol

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

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

There total 4 articles about N-(t-Butoxycarbonyl)-3-(4-methoxybenzyl)-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:

di-tert-butyl dicarbonate (24424-99-5) → N-(t-Butoxycarbonyl)-3-(4-methoxybenzyl)-L-histidine methyl ester (111102-62-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / triethylamine / methanol / 48 h / Ambient temperature

2: 1.) methanesulfonic anhydride, diisopropylethylamine / 1.) CH₂Cl₂, -50 deg C -> 0 deg C, 30 min, 2.) CH₂Cl₂, room temp., 22 h

With triethylamine; N-ethyl-N,N-diisopropylamine; Methanesulfonic anhydride; In methanol;

DOI:10.1055/s-1987-27828

Reference yield:

histidine methyl ester hydrochloride (4467-54-3,5619-10-3,7389-87-9,18684-16-7,22888-60-4,32381-17-2,92742-29-5,100009-20-9) → N-(t-Butoxycarbonyl)-3-(4-methoxybenzyl)-L-histidine methyl ester (111102-62-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / triethylamine / methanol / 48 h / Ambient temperature

2: 1.) methanesulfonic anhydride, diisopropylethylamine / 1.) CH₂Cl₂, -50 deg C -> 0 deg C, 30 min, 2.) CH₂Cl₂, room temp., 22 h

With triethylamine; N-ethyl-N,N-diisopropylamine; Methanesulfonic anhydride; In methanol;

DOI:10.1055/s-1987-27828

Reference yield:

4-Methoxybenzyl alcohol (105-13-5) + 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-methoxybenzyl)-L-histidine methyl ester (111102-62-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; Methanesulfonic anhydride; Yield given. Multistep reaction; 1.) CH2Cl2, -50 deg C -> 0 deg C, 30 min, 2.) CH2Cl2, room temp., 22 h;

DOI:10.1055/s-1987-27828

upstream raw materials:

4-Methoxybenzyl alcohol

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

Trifluoro-methanesulfonic acid 4-methoxy-benzyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

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

3-(4-Hydroxybenzyl)-L-histidine dihydrobromide

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