Pentanoic acid, 5-broMo-4-oxo-3-[[(2S)-1-oxo-2-[[(phenylMethoxy)carbonyl]aMino]propyl]aMino]-, 1,1-diMethylethyl ester, (3S)-

Base Information

• Chemical Name: Pentanoic acid, 5-broMo-4-oxo-3-[[(2S)-1-oxo-2-[[(phenylMethoxy)carbonyl]aMino]propyl]aMino]-, 1,1-diMethylethyl ester, (3S)-
• CAS No.: 868565-55-3
• Molecular Formula: C20H27BrN2O6
• Molecular Weight: 471.348
• Mol file: 868565-55-3.mol

Synonyms:Pentanoic acid, 5-broMo-4-oxo-3-[[(2S)-1-oxo-2-[[(phenylMethoxy)carbonyl]aMino]propyl]aMino]-, 1,1-diMethylethyl ester, (3S)-

Chemical Property of Pentanoic acid, 5-broMo-4-oxo-3-[[(2S)-1-oxo-2-[[(phenylMethoxy)carbonyl]aMino]propyl]aMino]-, 1,1-diMethylethyl ester, (3S)-

Chemical Property:

• PSA: 117.78000
• LogP: 3.52660

Purity/Quality:

≥95% ^*data from raw suppliers

Pentanoicacid,5-bromo-4-oxo-3-[[(2S)-1-oxo-2-[[(phenylmethoxy)carbonyl]amino]propyl]amino]-,1,1-dimethylethylester,(3S)- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Pentanoic acid, 5-broMo-4-oxo-3-[[(2S)-1-oxo-2-[[(phenylMethoxy)carbonyl]aMino]propyl]aMino]-, 1,1-diMethylethyl ester, (3S)-

There total 5 articles about Pentanoic acid, 5-broMo-4-oxo-3-[[(2S)-1-oxo-2-[[(phenylMethoxy)carbonyl]aMino]propyl]aMino]-, 1,1-diMethylethyl ester, (3S)- 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: 52.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + [(N-benzyloxycarbonyl)-L-alaninyl]-L-aspartic acid [beta]-tert-butyl ester (3408-50-2) → (3S)-3-[(N-benzyloxycarbonyl)-L-alaninyl]amino-5-bromo-4-oxopentanoic acid tert-butyl ester (868565-55-3)

Guidance literature:

[(N-benzyloxycarbonyl)-L-alaninyl]-L-aspartic acid [beta]-tert-butyl ester; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -10 ℃; for 0.333333h; Inert atmosphere;

diazomethane; In tetrahydrofuran; diethyl ether; at 0 - 20 ℃; for 0.75h; Inert atmosphere;

With hydrogen bromide; In tetrahydrofuran; diethyl ether; acetic acid; at 0 - 20 ℃; for 0.75h;

Reference yield:

(S)-3-((S)-2-Benzyloxycarbonylamino-propionylamino)-5-diazo-4-oxo-pentanoic acid tert-butyl ester → (3S)-3-[(N-benzyloxycarbonyl)-L-alaninyl]amino-5-bromo-4-oxopentanoic acid tert-butyl ester (868565-55-3)

Guidance literature:

With hydrogen bromide; acetic acid; In tetrahydrofuran; diethyl ether; at 0 - 20 ℃; for 0.75h;

DOI:10.1021/jm050307e

Reference yield:

L-Asp(t-Bu) (3057-74-7) → (3S)-3-[(N-benzyloxycarbonyl)-L-alaninyl]amino-5-bromo-4-oxopentanoic acid tert-butyl ester (868565-55-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: bis(trimethylsilyl)trifluoroacetamide / dimethylformamide / 0.5 h / 20 °C

1.2: 82 percent / dimethylformamide / 18 h / 20 °C

2.1: N-methylmorpholine; isobutyl chloroformate / tetrahydrofuran / 0.33 h / -10 °C

2.2: tetrahydrofuran; diethyl ether / 0.75 h / 0 - 20 °C

3.1: aq. HBr; AcOH / tetrahydrofuran; diethyl ether / 0.75 h / 0 - 20 °C

With 4-methyl-morpholine; bis(trimethylsilyl)trifluoroacetamide; hydrogen bromide; acetic acid; isobutyl chloroformate; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jm050307e

upstream raw materials:

L-Asp(t-Bu)

[(N-benzyloxycarbonyl)-L-alaninyl]-L-aspartic acid [beta]-tert-butyl ester

(N-benzyloxycarbonyl)-L-alanine N-hydroxysuccinimide ester

diazomethane