N-[(2'-Cyano[1,1'-biphenyl]-4-YL)methyl]-N-(1-oxopentyl)-L-valine methyl ester

Base Information

• Chemical Name: N-[(2'-Cyano[1,1'-biphenyl]-4-YL)methyl]-N-(1-oxopentyl)-L-valine methyl ester
• CAS No.: 137863-90-2
• Molecular Formula: C25H30N2O3
• Molecular Weight: 406.525
• European Community (EC) Number: 604-049-4
• UNII: 6X37Q93CWN
• DSSTox Substance ID: DTXSID801137642
• Nikkaji Number: J3.276.464I
• Mol file: 137863-90-2.mol

Synonyms:137863-90-2;Valsartan impurity F;6X37Q93CWN;N-[(2'-CYANO[1,1'-BIPHENYL]-4-YL)METHYL]-N-(1-OXOPENTYL)-L-VALINE METHYL ESTER;[N-(2-Cyanobiphenyl-4-yl)methyl]n-valery-(l)-valine methyl ester;UNII-6X37Q93CWN;methyl (2S)-2-[[4-(2-cyanophenyl)phenyl]methyl-pentanoylamino]-3-methylbutanoate;L-Valine, N-((2'-cyano(1,1'-biphenyl)-4-yl)methyl)-N-(1-oxopentyl)-, methyl ester;N-((2'-Cyano(1,1'-biphenyl)-4-yl)methyl)-N-(1-oxopentyl)-L-valine methyl ester;SUQNCOFVJNHEKQ-DEOSSOPVSA-N;SCHEMBL2033;DTXSID801137642;BCP15441;METHYL (2S)-2-[N-({2'-CYANO-[1,1'-BIPHENYL]-4-YL}METHYL)PENTANAMIDO]-3-METHYLBUTANOATE;AKOS015899761;N-[(2'-cyanobiphenyl-4-yl)methyl]-N-valeryl-(L)-valine methylester;N-[(2'-cyanobiphenyl-4-yl)-methyl]-N-valeryl-(L)-valine methyl ester;N-[(2'-cyanobiphenyl-4-yl)methyl]-N-valeryl-(L)-valine methyl ester;N-valeryl-N-[(2'-cyanobiphenyl-4-yl)methyl]-(L)-valine methyl ester;(S)-2-[(2'-cyano-biphenyl-4-ylmethyl)-pentanoyl-amino]-3-methyl-butyric acid methyl ester;(S)-Methyl 2-(N-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)pentanamido)-3-methylbutanoate;N-[(2'-Cyano[1,1'-biphenyl]-4-yl)methyl]-N-pentanoyl-L-valine Methyl Ester;N-[(2'-CYANOBIPHENYL4-YL)-METHYL]-N-VALERYL-(L)-VALINE METHYL ESTER;N-[(2a(2)-Cyano[1,1a(2)-biphenyl]-4-yl)methyl]-N-(1-oxopentyl)-L-valine methyl ester;L-Valine, N-[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]-N-(1-oxopentyl)-, methyl ester;N-[(2'-Cyano[1,1'-biphenyl]-4-yl)methyl]-N-(1-oxopentyl)-L-valine methyl ester

Chemical Property of N-[(2'-Cyano[1,1'-biphenyl]-4-YL)methyl]-N-(1-oxopentyl)-L-valine methyl ester

Chemical Property:

• Boiling Point: 579.3±50.0 °C(Predicted)
• PKA: -0.99±0.70(Predicted)
• PSA: 70.40000
• Density: 1.12±0.1 g/cm3(Predicted)
• LogP: 4.94168
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (slightly)
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 406.22564282
• Heavy Atom Count: 30
• Complexity: 601

Purity/Quality:

99% ^*data from raw suppliers

N-[(2''-Cyano[1,1''-biphenyl]-4-yl)methyl]-N-(1-oxopentyl)-L-valineMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(=O)N(CC1=CC=C(C=C1)C2=CC=CC=C2C#N)C(C(C)C)C(=O)OC
• Isomeric SMILES: CCCCC(=O)N(CC1=CC=C(C=C1)C2=CC=CC=C2C#N)[C@@H](C(C)C)C(=O)OC
• Uses: N-[(2''-Cyano[1,1''-biphenyl]-4-yl)methyl]-N-(1-oxopentyl)-L-valine Methyl Ester is an impurity of the drug Valsartan (V095750), which is a nonpeptide angiotensin II AT1-receptor antagonist. Antihypertensive.

Technology Process of N-[(2'-Cyano[1,1'-biphenyl]-4-YL)methyl]-N-(1-oxopentyl)-L-valine methyl ester

There total 30 articles about N-[(2'-Cyano[1,1'-biphenyl]-4-YL)methyl]-N-(1-oxopentyl)-L-valine methyl ester 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: 99.2%

N-((2'-cyano[1,1'-biphenyl]-4-yl)methyl)-L-valine methyl ester hydrochloride (482577-59-3) + n-valeryl chloride (638-29-9) → methyl 2-(N-((2'-cyanobiphenyl-4-yl)methyl)pentanamido)-3-methylbutanoate (137863-90-2)

Guidance literature:

With potassium carbonate; sodium chloride; In 5,5-dimethyl-1,3-cyclohexadiene; water; at 20 - 28 ℃; Solvent; Reagent/catalyst;

Reference yield: 98.0%

N-[(2'-cyanobiphenyl-4-yl)-methyl]-(L)-valine methyl ester (137863-89-9) + n-valeryl chloride (638-29-9) → methyl 2-(N-((2'-cyanobiphenyl-4-yl)methyl)pentanamido)-3-methylbutanoate (137863-90-2)

Guidance literature:

With pyridine; In dichloromethane; at 40 ℃; for 2h;

DOI:10.1021/jo701391q

Reference yield: 92.0%

N-pentanoyl-N-[4-(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaborolan-2'-yl)benzyl]-L-valinemethyl ester (883223-09-4) + o-cyanobromobenzene (2042-37-7) → methyl 2-(N-((2'-cyanobiphenyl-4-yl)methyl)pentanamido)-3-methylbutanoate (137863-90-2)

Guidance literature:

With caesium carbonate; In water; N,N-dimethyl-formamide; at 50 ℃; for 2h;

DOI:10.1002/adsc.201300499

upstream raw materials:

N-[(2'-cyanobiphenyl-4-yl)-methyl]-(L)-valine methyl ester

n-valeryl chloride

C₁₆H₁₃O₂N

p-bromobenzaldehyde 1,3-dioxolane

Downstream raw materials:

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

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

Refernces

• 1、 -. "Synthesis method of valsartan intermediate". Paragraph 0006; 0028-0039. . Retrieved 2019/09/17.
• 2、 -. "A method of preparing the valsartan". . . Retrieved 2017/02/24.