(S)-2-(2-(((Benzyloxy)carbonyl)amino)acetamido)-3-methylbutanoic acid

Base Information

• Chemical Name: (S)-2-(2-(((Benzyloxy)carbonyl)amino)acetamido)-3-methylbutanoic acid
• CAS No.: 33912-87-7
• Molecular Formula: C15H20 N2 O5
• Molecular Weight: 308.334
• Hs Code.: 2924299090
• European Community (EC) Number: 251-741-3
• Nikkaji Number: J287.824K
• Mol file: 33912-87-7.mol

Synonyms:33912-87-7;(S)-2-(2-(((Benzyloxy)carbonyl)amino)acetamido)-3-methylbutanoic acid;Z-Gly-Val-OH;C15H20N2O5;(2S)-3-methyl-2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]butanoic acid;SCHEMBL4582904;RQLYPCLOROQBGI-ZDUSSCGKSA-N;N-(Benzyloxycarbonyl)-Gly-Val-OH;((benzyloxy)carbonyl)glycyl-L-valine;(S)-2-(2-(((Benzyloxy)carbonyl)amino)acetamido)-3-methylbutanoicacid;(2S)-2-(2-{[(BENZYLOXY)CARBONYL]AMINO}ACETAMIDO)-3-METHYLBUTANOIC ACID

Chemical Property of (S)-2-(2-(((Benzyloxy)carbonyl)amino)acetamido)-3-methylbutanoic acid

Chemical Property:

• Vapor Pressure: 3.73E-14mmHg at 25°C
• Boiling Point: 577°Cat760mmHg
• Flash Point: 302.8°C
• PSA: 104.73000
• Density: 1.226g/cm³
• LogP: 1.92000
• Storage Temp.: -15°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 308.13722174
• Heavy Atom Count: 22
• Complexity: 391

Purity/Quality:

99% ^*data from raw suppliers

N-(Benzyloxycarbonyl)glycyl-L-valine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)O)NC(=O)CNC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)[C@@H](C(=O)O)NC(=O)CNC(=O)OCC1=CC=CC=C1
• Uses: N-(Benzyloxycarbonyl)glycyl-L-valine has been used as a reactant for the preparation of retroviral protease inhibitors. N-(Benzyloxycarbonyl)glycyl-L-valine has also been used as a reactant for the synthesis of benzimidazole derivatives.

Technology Process of (S)-2-(2-(((Benzyloxy)carbonyl)amino)acetamido)-3-methylbutanoic acid

There total 7 articles about (S)-2-(2-(((Benzyloxy)carbonyl)amino)acetamido)-3-methylbutanoic 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: 97.0%

L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + perfluorophenyl 2-(((benzyloxy)carbonyl)amino)acetate (16748-79-1) → N-benzyloxycarbonylglycyl-L-valine (Z-Gly-Val) (33912-87-7)

Guidance literature:

With calcium perchlorate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

Reference yield: 72.0%

(S)-methyl 2-(2-(benzyloxycarbonylamino)acetamido)-3-methyl butanoate (61058-41-1) → N-benzyloxycarbonylglycyl-L-valine (Z-Gly-Val) (33912-87-7)

Guidance literature:

With sodium hydroxide; In water; acetone;

DOI:10.1021/acs.jmedchem.6b00134

Reference yield:

N-(Benzyloxycarbonyl)glycine (1138-80-3) → N-benzyloxycarbonylglycyl-L-valine (Z-Gly-Val) (33912-87-7)

Guidance literature:

Multi-step reaction with 2 steps

1: dicyclohexylcarbodiimide / polymer-bound 4-dialkylaminopyridine 2 / CH₂Cl₂ / 1) 0 deg C, 15 min, 2) r.t., 3 h

2: NaOH / methanol

With sodium hydroxide; dicyclohexyl-carbodiimide; polymer-bound 4-dialkylaminopyridine 2; In methanol; dichloromethane;

upstream raw materials:

(S)-methyl 2-(2-(benzyloxycarbonylamino)acetamido)-3-methyl butanoate

L-valine

perfluorophenyl 2-(((benzyloxy)carbonyl)amino)acetate

L-Valine methyl ester

Downstream raw materials:

Z-Gly-D-Val-Val-OMe

Z-Gly-Val-Val-OMe

Z-Gly-Val-Leu-OMe

(S)-2-[(R)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-4-methyl-pentanoic acid methyl ester