(S)-2-((S)-2-(((benzyloxy)carbonyl)amino)propanamido)-3-(((S)-2-(((tert-butoxy)carbonyl)amino)-3-phenylpropanoyl)oxy)propanoic acid

Base Information

• Chemical Name: (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)propanamido)-3-(((S)-2-(((tert-butoxy)carbonyl)amino)-3-phenylpropanoyl)oxy)propanoic acid
• CAS No.: 1380521-32-3
• Molecular Formula: C₂₈H₃₅N₃O₉
• Molecular Weight: 557.601
• Mol file: 1380521-32-3.mol

Synonyms:(S)-2-((S)-2-(((benzyloxy)carbonyl)amino)propanamido)-3-(((S)-2-(((tert-butoxy)carbonyl)amino)-3-phenylpropanoyl)oxy)propanoic acid

Chemical Property of (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)propanamido)-3-(((S)-2-(((tert-butoxy)carbonyl)amino)-3-phenylpropanoyl)oxy)propanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)propanamido)-3-(((S)-2-(((tert-butoxy)carbonyl)amino)-3-phenylpropanoyl)oxy)propanoic acid

There total 6 articles about (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)propanamido)-3-(((S)-2-(((tert-butoxy)carbonyl)amino)-3-phenylpropanoyl)oxy)propanoic acid 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: 73.0%

(2S)-2-[((2S)-2-{[(benzyloxy)carbonyl]amino}propanoyl)amino]-3-hydroxypropanoic acid (17460-58-1,109337-83-9,41864-10-2) + (S)-tert-butyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate (514214-66-5) → (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)propanamido)-3-(((S)-2-(((tert-butoxy)carbonyl)amino)-3-phenylpropanoyl)oxy)propanoic acid (1380521-32-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 12h;

DOI:10.3998/ark.5550190.p008.632

Reference yield: 70.0%

(S)-2-((S)-2-(((tert-butoxy)carbonyl)amino)-3-phenylpropanamido)-3-hydroxypropanoic acid (123228-32-0) + benzyl N-[(1S)-2-(1H-1,2,3-benzotriazol-1-yl)-1-methyl-2-oxoethyl]carbamate (820239-42-7) → (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)propanamido)-3-(((S)-2-(((tert-butoxy)carbonyl)amino)-3-phenylpropanoyl)oxy)propanoic acid (1380521-32-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 12h;

DOI:10.1039/c2ob07050b

Reference yield:

N-Cbz-Ala (1142-20-7) → (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)propanamido)-3-(((S)-2-(((tert-butoxy)carbonyl)amino)-3-phenylpropanoyl)oxy)propanoic acid (1380521-32-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: thionyl chloride / dichloromethane / 0.25 h / 20 °C

1.2: 2.5 h / 20 °C

2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 12 h / 20 °C

With thionyl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile;

DOI:10.1039/c2ob07050b

upstream raw materials:

N-Cbz-Ala

N-tert-butoxycarbonyl-L-phenylalanine

(S)-2-((S)-2-(((tert-butoxy)carbonyl)amino)-3-phenylpropanamido)-3-hydroxypropanoic acid

benzyl N-[(1S)-2-(1H-1,2,3-benzotriazol-1-yl)-1-methyl-2-oxoethyl]carbamate

Downstream raw materials:

C₂₀H₂₉N₃O₇