Valesteramide

Base Information

• Chemical Name: Valesteramide
• CAS No.: 137864-22-3
• Molecular Formula: C31H34N2O3
• Molecular Weight: 482.623
• Mol file: 137864-22-3.mol

Synonyms:N-[2'-cyano-biphenyl-4-yl methyl]-N-valeryl-(L)-valine benzyl ester;

Chemical Property of Valesteramide

Chemical Property:

• Boiling Point: 657.065 °C at 760 mmHg
• Flash Point: 351.181 °C
• Density: 1.147 g/cm³

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Valesteramide

There total 7 articles about Valesteramide 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: 72.0%

n-valeryl chloride (638-29-9) + (S)-N-[(2'-Cyano-biphenyl-4-yl)methyl]valine benzyl ester (137864-23-4) → (S)-2-[(2'-cyanobiphenyl-4-ylmethyl)pentanoylamino]-3-methylbutyric acid benzyl ester (137864-22-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 20 - 25h; Product distribution / selectivity;

Reference yield:

N-[(2'-cyanobiphenyl-4-yl)methyl]-(L)-valine benzyl ester hydrochloride + n-valeryl chloride (638-29-9) → (S)-2-[(2'-cyanobiphenyl-4-ylmethyl)pentanoylamino]-3-methylbutyric acid benzyl ester (137864-22-3)

Guidance literature:

With sodium carbonate; In dichloromethane;

Reference yield:

2-Cyano-4'-methylbiphenyl (114772-53-1) → (S)-2-[(2'-cyanobiphenyl-4-ylmethyl)pentanoylamino]-3-methylbutyric acid benzyl ester (137864-22-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-Bromosuccinimide; hydrogen bromide; 2,2'-azobis(isobutyronitrile) / water; cyclohexane / 3 h / 65 - 68 °C

2.1: sodium hydroxide / water; 5,5-dimethyl-1,3-cyclohexadiene / 20 °C / pH < 8.5 - 9 / Large scale

2.2: 3.42 h / 60 °C / Large scale

2.3: 2 h / 72 °C / Dean-Stark; Large scale

3.1: sodium hydroxide / water; 5,5-dimethyl-1,3-cyclohexadiene / 0.5 h / 50 °C

3.2: 2 h / 40 °C

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); hydrogen bromide; sodium hydroxide; In 5,5-dimethyl-1,3-cyclohexadiene; cyclohexane; water; 3.1: |Schotten-Baumann Reaction / 3.2: |Schotten-Baumann Reaction;

DOI:10.1021/op700120n

upstream raw materials:

n-valeryl chloride

(S)-N-[(2'-Cyano-biphenyl-4-yl)methyl]valine benzyl ester

2-Cyano-4'-methylbiphenyl

L-valine benzyl ester

Downstream raw materials:

(S)-N-(1-benzyloxycarbonyl-2-methyl-prop-1-yl)-N-pentanoyl-N-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amine

N-((2'-(cyano)-[1,1'-biphenyl]-4-yl)methyl)-N-pentanoyl-L-valine

C₃₃H₃₆N₂O₃

C₁₂H₂₃N*C₂₄H₂₈N₂O₃

Refernces

• 1、 -. "PROCESS FOR PREPARATION OF 5-SUBSTITUTED TETRAZOLES". Page/Page column 15. . Retrieved 2010/12/18.
• 2、 Beutler, Ulrich,Boehm, Matthias,Fuenfschilling, Peter C.,Heinz, Thomas,Mutz, Jean-Paul,Onken, Ulrich,Mueller, Martin,Zaugg, Werner. "A high-throughput process for valsartan". . p. 892 - 898. Retrieved 2012/12/30.