(S)-Methyl 2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)-3-methylbutanoate

Base Information

• Chemical Name: (S)-Methyl 2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)-3-methylbutanoate
• CAS No.: 137863-89-9
• Molecular Formula: C20H22N2O2
• Molecular Weight: 322.407
• Hs Code.: 2926909090
• European Community (EC) Number: 604-048-9
• UNII: 13EG6HX8ND
• DSSTox Substance ID: DTXSID50587775
• Nikkaji Number: J2.513.903H
• Wikidata: Q27251511
• Mol file: 137863-89-9.mol

Synonyms:137863-89-9;(S)-Methyl 2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)-3-methylbutanoate;Valsartan impurity D;N-[(2'-Cyano-(1,1'-biphenyl)-4-yl)methyl)]valine methyl ester;13EG6HX8ND;methyl (2S)-2-[[4-(2-cyanophenyl)phenyl]methylamino]-3-methylbutanoate;N-((2'-Cyano(1,1'-biphenyl)-4-yl)methyl)-L-valine methyl ester;L-Valine, N-((2'-cyano(1,1'-biphenyl)-4-yl)methyl)-, methyl ester;methyl ((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-L-valinate;UNII-13EG6HX8ND;Methyl N-[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]-L-valinate;METHYL N-((2'-CYANO(1,1'-BIPHENYL)-4-YL)METHYL)-L-VALINATE;Valsartan impurity D [USP-MC];SCHEMBL2174;DTXSID50587775;METHYL (2S)-2-[({2'-CYANO-[1,1'-BIPHENYL]-4-YL}METHYL)AMINO]-3-METHYLBUTANOATE;ZQHINOUCNQKQEV-IBGZPJMESA-N;AKOS015850911;A886380;Q27251511;N-[(2'-cyanobiphenyl-4-yl)methyl]-(L)-valine methyl ester;N-[(2'-cyanobiphenyl-4-yl)methyl]-(L)-valine methylester;N-[(2'-cyanobiphenyl-4-yl) methyl]-(L)-valine methyl ester;N-[(2'-Cyano[1,1-biphenyl]-4-yl)methyl]-L-valine methylester;(S)-METHYL 2-((2'-CYANOBIPHENYL-4-YL)METHYLAMINO)-3-METHYLBUTANOATE;(S)-Methyl2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)-3-methylbutanoate

Chemical Property of (S)-Methyl 2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)-3-methylbutanoate

Chemical Property:

• Boiling Point: 477.9 °C at 760 mmHg
• PKA: 6.10±0.40(Predicted)
• Flash Point: 242.8 °C
• PSA: 62.12000
• Density: 1.12 g/cm³
• LogP: 3.90338
• Storage Temp.: 2-8°C
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 322.168127949
• Heavy Atom Count: 24
• Complexity: 446

Purity/Quality:

99% ^*data from raw suppliers

(S)-Methyl2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)-3-methylbutanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)OC)NCC1=CC=C(C=C1)C2=CC=CC=C2C#N
• Isomeric SMILES: CC(C)[C@@H](C(=O)OC)NCC1=CC=C(C=C1)C2=CC=CC=C2C#N
• Uses: N-[(2'-Cyano[1,1'-biphenyl]-4-yl)methyl]-L-valine Methyl Ester is an intermediate in the preparation of angiotensin II type 1 receptor antagonists.

Technology Process of (S)-Methyl 2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)-3-methylbutanoate

There total 12 articles about (S)-Methyl 2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)-3-methylbutanoate 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: 90.0%

L-valine methylester hydrochloride (6306-52-1) + 4-(2-Cyanophenyl)benzaldehyde (135689-93-9) → N-[(2'-cyanobiphenyl-4-yl)-methyl]-(L)-valine methyl ester (137863-89-9)

Guidance literature:

L-valine methylester hydrochloride; 4-(2-Cyanophenyl)benzaldehyde; With 3 A molecular sieve; In tetrahydrofuran; at 20 ℃; for 60h;

With sodium cyanoborohydride; In tetrahydrofuran; ethanol; at 23 ℃; for 24h; Further stages.;

DOI:10.1021/jo701391q

Reference yield: 81.8%

L-valine methylester hydrochloride (6306-52-1) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → N-[(2'-cyanobiphenyl-4-yl)-methyl]-(L)-valine methyl ester (137863-89-9)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 70 ℃; Inert atmosphere; Cooling with ice;

DOI:10.1016/j.bmc.2012.02.003

Reference yield:

N-((2'-cyano[1,1'-biphenyl]-4-yl)methyl)-L-valine methyl ester hydrochloride (482577-59-3) → N-[(2'-cyanobiphenyl-4-yl)-methyl]-(L)-valine methyl ester (137863-89-9)

Guidance literature:

With sodium hydrogencarbonate; In water; xylene; at 25 - 30 ℃; for 0.5h;

upstream raw materials:

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

L-valine methylester hydrochloride

4-(2-Cyanophenyl)benzaldehyde

C₁₆H₁₃O₂N

Downstream raw materials:

methyl 2-(N-((2'-cyanobiphenyl-4-yl)methyl)pentanamido)-3-methylbutanoate

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

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

N-(1-oxopentyl)-n-[[2'-(2-tributyltintetrazol-5-yl)-(1,1'-biphenyl)-4-yl]methyl]-(L)-valine methyl ester

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF VALSARTAN". Paragraph 0053; 0054; 0055. . Retrieved 2013/06/26.
• 2、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF VALSARTAN". Page/Page column 14-15. . Retrieved 2012/01/14.