2-benzyl-5-cyano-4-oxopentanoic acid

Base Information

• Chemical Name: 2-benzyl-5-cyano-4-oxopentanoic acid
• CAS No.: 126121-83-3
• Molecular Formula: C13H13 N O3
• Molecular Weight: 231.2472
• Mol file: 126121-83-3.mol

Synonyms:Benzenepropanoic acid,a-(3-cyano-2-oxopropyl)-,(R)-(9CI);

Chemical Property of 2-benzyl-5-cyano-4-oxopentanoic acid

Chemical Property:

• Vapor Pressure: 5.55E-08mmHg at 25°C
• Boiling Point: 425°Cat760mmHg
• Flash Point: 210.9°C
• PSA: 78.16000
• Density: 1.215g/cm³
• LogP: 1.80278

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-benzyl-5-cyano-4-oxopentanoic acid

There total 1 articles about 2-benzyl-5-cyano-4-oxopentanoic 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:

dimethyl (R)-(+)-benzylsuccinate (130272-52-5) + acetonitrile (75-05-8,26809-02-9) → (R)-2-benzyl-5-cyano-4-oxopentanoic acid (126121-83-3)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C, 1 h, then 0 deg C, 0.5 h;

DOI:10.1021/jm00100a024

Reference yield: 49.0%

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + (R)-2-benzyl-5-cyano-4-oxopentanoic acid (126121-83-3) → N-<(R)-2-benzyl-5-cyano-4-oxopentanoyl>-L-phenylalanine methyl ester (136282-52-5)

Guidance literature:

With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 23 ℃; for 12h;

DOI:10.1021/jm00100a024

Reference yield:

(R)-2-benzyl-5-cyano-4-oxopentanoic acid (126121-83-3) → N-<(R)-2-benzyl-5-cyano-4-oxopentanoyl>-L-phenylalanine (136282-56-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / Et₃N, 1-hydroxybenzotriazole hydrate (HOBt), 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDC) / dimethylformamide / 12 h / 23 °C

2: 66 percent / NaOH / methanol; H₂O

With sodium hydroxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00100a024

upstream raw materials:

dimethyl (R)-(+)-benzylsuccinate

acetonitrile

Downstream raw materials:

N-<(R)-2-benzyl-5-cyano-4-oxopentanoyl>-L-phenylalanine methyl ester

N-<(R)-2-benzyl-5-cyano-4-oxopentanoyl>-L-phenylalanine

Refernces