(2S)-2-[(2-[[(benzyloxy)carbonyl]amino]-2-methylpropanoyl)amino]-3-phenylpropanoic acid

Base Information

• Chemical Name: (2S)-2-[(2-[[(benzyloxy)carbonyl]amino]-2-methylpropanoyl)amino]-3-phenylpropanoic acid
• CAS No.: 3350-43-4
• Molecular Formula: C₂₁H₂₄N₂O₅
• Molecular Weight: 384.432

Synonyms:(2S)-2-[(2-[[(benzyloxy)carbonyl]amino]-2-methylpropanoyl)amino]-3-phenylpropanoic acid

Chemical Property of (2S)-2-[(2-[[(benzyloxy)carbonyl]amino]-2-methylpropanoyl)amino]-3-phenylpropanoic acid

Chemical Property:

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Technology Process of (2S)-2-[(2-[[(benzyloxy)carbonyl]amino]-2-methylpropanoyl)amino]-3-phenylpropanoic acid

There total 9 articles about (2S)-2-[(2-[[(benzyloxy)carbonyl]amino]-2-methylpropanoyl)amino]-3-phenylpropanoic 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: 100.0%

Z-AIB-(L)-Phe-O-(t-Bu) (152972-10-6) → (2S)-2-[(2-[[(benzyloxy)carbonyl]amino]-2-methylpropanoyl)amino]-3-phenylpropanoic acid (3350-43-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 16h;

DOI:10.1016/S0040-4020(01)88010-8

Reference yield: 84.0%

benzyl N-[2-(1H-1,2,3-benzotriazol-1-yl)-1,1-dimethyl-2-oxoethyl]carbamate + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → (2S)-2-[(2-[[(benzyloxy)carbonyl]amino]-2-methylpropanoyl)amino]-3-phenylpropanoic acid (3350-43-4)

Guidance literature:

With triethylamine; In water; acetonitrile; at 20 ℃; for 1h;

DOI:10.1021/jo0704255

Reference yield:

Z-Aib-OH (15030-72-5) → (2S)-2-[(2-[[(benzyloxy)carbonyl]amino]-2-methylpropanoyl)amino]-3-phenylpropanoic acid (3350-43-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / DCC, 1-hydroxybenzotriazole / tetrahydrofuran / 24 h

2: 100 percent / TFA / CH₂Cl₂ / 16 h

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(01)88010-8

upstream raw materials:

Z-AIB-(L)-Phe-O-(t-Bu)

2-(benzyloxycarbonylamino)isobutyryl-L-phenylalanine methyl ester

L-phenylalanine

Z-Aib-OH

Downstream raw materials:

[1-((S)-4-benzyl-5-oxo-4,5-dihydro-oxazol-2-yl)-1-methyl-ethyl]-carbamic acid benzyl ester

Z-AIB-(L)-Phe-(D)-Pro-OMe

(R)-1-{(S)-2-[2-((S)-2-Benzyloxycarbonylamino-5-chloro-pentanoylamino)-2-methyl-propionylamino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid pentafluorophenyl ester

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