benzyl (3S)-5-bromo-3-(tert-butoxycarbonylamino)-4-oxo-pentanoate

Base Information

• Chemical Name: benzyl (3S)-5-bromo-3-(tert-butoxycarbonylamino)-4-oxo-pentanoate
• CAS No.: 189580-34-5
• Molecular Formula: C17H22BrNO5
• Mol file: 189580-34-5.mol

Synonyms:

Chemical Property of benzyl (3S)-5-bromo-3-(tert-butoxycarbonylamino)-4-oxo-pentanoate

Chemical Property:

• Vapor Pressure: 7.52E-11mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (3S)-5-bromo-3-(tert-butoxycarbonylamino)-4-oxo-pentanoate

There total 4 articles about benzyl (3S)-5-bromo-3-(tert-butoxycarbonylamino)-4-oxo-pentanoate 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:

diazomethane (186581-53-3,908094-01-9,334-88-3) + BOC-L-aspartic acid 4-benzyl ester (7536-58-5,98482-77-0) → Boc-L-ASP(Bzl)-BMK (189580-34-5)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1016/S0040-4020(97)00195-6

Reference yield:

benzyl (S)-3-<(tert-butoxy)carbonylamino>-5-diazo-4-oxopentanoate → Boc-L-ASP(Bzl)-BMK (189580-34-5)

Guidance literature:

With hydrogen bromide; In tetrahydrofuran; water; at 20 ℃; for 0.0833333h;

DOI:10.2174/092986612799363172

Reference yield:

(S)-3-tert-Butoxycarbonylamino-4-ethoxycarbonyloxy-4-oxo-butyric acid benzyl ester → Boc-L-ASP(Bzl)-BMK (189580-34-5)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran; diethyl ether / -15 °C

2: hydrogen bromide / tetrahydrofuran; water / 0.08 h / 20 °C

With hydrogen bromide; In tetrahydrofuran; diethyl ether; water;

DOI:10.2174/092986612799363172

upstream raw materials:

diazomethane

BOC-L-aspartic acid 4-benzyl ester

Downstream raw materials:

C₂₃H₂₃F₄NO₆

Refernces

• 1、 -. "A CRYSTAL OF A CASPASE INHIBITOR". Paragraph 0120-0121. . Retrieved 2021/01/26.
• 2、 Albeck, Amnon,Estreicher, Gary I.. "FunctionaIized erythro N-protected α-amino epoxides. Stereocontrolled synthesis and biological activity". . p. 5325 - 5338. Retrieved 2007/10/03.