N-[[(1S)-1-[(benzyloxy)carbonyl]ethyl]carbamoyl]-L-tryptophan tert-butylester

Base Information

• Chemical Name: N-[[(1S)-1-[(benzyloxy)carbonyl]ethyl]carbamoyl]-L-tryptophan tert-butylester
• CAS No.: 286939-23-9
• Molecular Formula: C₂₆H₃₁N₃O₅
• Molecular Weight: 465.549
• Mol file: 286939-23-9.mol

Synonyms:N-[[(1S)-1-[(benzyloxy)carbonyl]ethyl]carbamoyl]-L-tryptophan tert-butylester

Chemical Property of N-[[(1S)-1-[(benzyloxy)carbonyl]ethyl]carbamoyl]-L-tryptophan tert-butylester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[[(1S)-1-[(benzyloxy)carbonyl]ethyl]carbamoyl]-L-tryptophan tert-butylester

There total 1 articles about N-[[(1S)-1-[(benzyloxy)carbonyl]ethyl]carbamoyl]-L-tryptophan tert-butylester 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: 88.0%

bis(trichloromethyl) carbonate (32315-10-9) + L-alanine benzyl ester p-toluenesulfonate (42854-62-6) + L-tryptophan tert-butyl ester hydrochloride → N-[[(1S)-1-[(benzyloxy)carbonyl]ethyl]carbamoyl]-L-tryptophan tert-butylester (286939-23-9)

Guidance literature:

bis(trichloromethyl) carbonate; L-alanine benzyl ester p-toluenesulfonate; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.0833333h;

L-tryptophan tert-butyl ester hydrochloride; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.5h; Further stages.;

DOI:10.1021/ja003292c

Reference yield:

N-[[(1S)-1-[(benzyloxy)carbonyl]ethyl]carbamoyl]-L-tryptophan tert-butylester (286939-23-9) → N-[[(1S)-1-[(pentafluorophenoxy)carbonyl]ethyl]carbamoyl]-L-tryptophan tert-butyl ester (286939-25-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 78 percent / H₂ / Pd/C / methanol / 5 h / 20 °C / 760.05 Torr

2.1: DCC / ethyl acetate / 1 h / 0 °C

2.2: 92 percent / ethyl acetate / 0.5 h / 20 °C

With hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; ethyl acetate;

DOI:10.1021/ja003292c

upstream raw materials:

bis(trichloromethyl) carbonate

L-alanine benzyl ester p-toluenesulfonate

Downstream raw materials:

N-[[(1S)-1-[(pentafluorophenoxy)carbonyl]ethyl]carbamoyl]-L-tryptophan tert-butyl ester