(S)-2-[(2'-cyanobiphenyl-4-ylmethyl)amino]-3-methylbutyric acid benzyl ester hydrochloride

Base Information

• Chemical Name: (S)-2-[(2'-cyanobiphenyl-4-ylmethyl)amino]-3-methylbutyric acid benzyl ester hydrochloride
• CAS No.: 137864-24-5
• Molecular Formula: C₂₆H₂₆N₂O₂*ClH
• Molecular Weight: 434.966
• Mol file: 137864-24-5.mol

Synonyms:(S)-2-[(2'-cyanobiphenyl-4-ylmethyl)amino]-3-methylbutyric acid benzyl ester hydrochloride

Chemical Property of (S)-2-[(2'-cyanobiphenyl-4-ylmethyl)amino]-3-methylbutyric acid benzyl ester hydrochloride

Chemical Property:

Purity/Quality:

90%，95%，97%，98%，99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-2-[(2'-cyanobiphenyl-4-ylmethyl)amino]-3-methylbutyric acid benzyl ester hydrochloride

There total 4 articles about (S)-2-[(2'-cyanobiphenyl-4-ylmethyl)amino]-3-methylbutyric acid benzyl ester hydrochloride 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: 98.0%

L-valine benzyl ester p-toluenesulfonate salt (16652-76-9) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → (S)-2-[(2'-cyanobiphenyl-4-ylmethyl)amino]-3-methylbutyric acid benzyl ester hydrochloride (137864-24-5)

Guidance literature:

L-valine benzyl ester p-toluenesulfonate salt; With sodium hydroxide; In 5,5-dimethyl-1,3-cyclohexadiene; water; at 20 ℃; pH=< 8.5 - 9; Large scale;

4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile; In 5,5-dimethyl-1,3-cyclohexadiene; at 60 ℃; for 3.41667h; Large scale;

With hydrogenchloride; In 5,5-dimethyl-1,3-cyclohexadiene; water; at 72 ℃; for 2h; Dean-Stark; Large scale;

DOI:10.1021/op700120n

Reference yield:

L-valine benzyl ester (21760-98-5) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → (S)-2-[(2'-cyanobiphenyl-4-ylmethyl)amino]-3-methylbutyric acid benzyl ester hydrochloride (137864-24-5)

Guidance literature:

L-valine benzyl ester; 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile; With sodium carbonate; In ethyl acetate; at 70 ℃; for 16h; Reflux;

With hydrogenchloride; In ethyl acetate; at 5 ℃; for 2h; pH=1.5 - 2; Product distribution / selectivity;

Reference yield:

2-Cyano-4'-methylbiphenyl (114772-53-1) → (S)-2-[(2'-cyanobiphenyl-4-ylmethyl)amino]-3-methylbutyric acid benzyl ester hydrochloride (137864-24-5)

Guidance literature:

Multi-step reaction with 2 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

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); hydrogen bromide; sodium hydroxide; In 5,5-dimethyl-1,3-cyclohexadiene; cyclohexane; water;

DOI:10.1021/op700120n

upstream raw materials:

L-valine benzyl ester p-toluenesulfonate salt

4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile

L-valine benzyl ester

2-Cyano-4'-methylbiphenyl

Downstream raw materials:

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

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

N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine