(2R)-2-((2S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-hydroxypropanoic acid

Base Information

• Chemical Name: (2R)-2-((2S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-hydroxypropanoic acid
• CAS No.: 17460-68-3
• Molecular Formula: C₂₀H₂₂N₂O₆
• Molecular Weight: 386.404
• Mol file: 17460-68-3.mol

Synonyms:(2R)-2-((2S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-hydroxypropanoic acid

Chemical Property of (2R)-2-((2S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-hydroxypropanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-2-((2S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-hydroxypropanoic acid

There total 3 articles about (2R)-2-((2S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-hydroxypropanoic 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: 87.0%

D-Serine (312-84-5,83245-15-2) + (S)-benzyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate (769922-77-2) → (2R)-2-((2S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-hydroxypropanoic acid (17460-68-3)

Guidance literature:

With triethylamine; In water; acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2015.05.020

Reference yield:

N-Cbz-L-Phe (1161-13-3) → (2R)-2-((2S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-hydroxypropanoic acid (17460-68-3)

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: triethylamine / water; acetonitrile / 2 h / 20 °C

With thionyl chloride; triethylamine; In dichloromethane; water; acetonitrile;

DOI:10.1016/j.bmcl.2015.05.020

Reference yield:

N-Cbz-L-Phe (1161-13-3) + R-(-)-serine methyl ester hydrochloride (5874-57-7) → (2R)-2-((2S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-hydroxypropanoic acid (17460-68-3)

Guidance literature:

Multistep reaction; (i) ClCO₂Et, Et₃N, (ii) /BRN= 4236602/, Et₃N, (iii) aq. NaOH;

DOI:10.1021/jm00307a016

upstream raw materials:

N-Cbz-L-Phe

R-(-)-serine methyl ester hydrochloride

D-Serine

(S)-benzyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate