(R)-2-(N-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)pentanamido)-3-methylbutanoic acid

Base Information

• Chemical Name: (R)-2-(N-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)pentanamido)-3-methylbutanoic acid
• CAS No.: 137862-87-4
• Molecular Formula: C₂₄H₂₉N₅O₃
• Molecular Weight: 435.526
• Hs Code.: 2933997500
• European Community (EC) Number: 810-430-8
• UNII: IDC67444MI
• Nikkaji Number: J788.652G
• Wikidata: Q27280672
• ChEMBL ID: CHEMBL115622
• Mol file: 137862-87-4.mol

Synonyms:137862-87-4;D-Valsartan;(R)-2-(N-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)pentanamido)-3-methylbutanoic acid;Valsartan, D-;ent-Valsartan;CGP-49309;UNII-IDC67444MI;CHEMBL115622;IDC67444MI;Valsartan specified impurity A [EP];(2R)-3-methyl-2-[pentanoyl-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]amino]butanoic acid;(2R)-3-Methyl-2-(pentanoyl((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)amino)butanoic acid;(2R)-3-methyl-2-[pentanoyl-[[4-[2-(1H-tetrazol-5-yl)phenyl]phenyl]methyl]amino]butanoic acid;D-Valine, N-(1-oxopentyl)-N-((2'-(2H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-;DTXCID603735;R-Valsartan;NCGC00095139-01;Valsartan EP impurity A;SCHEMBL2328;SCHEMBL24722321;(2R)-3-Methyl-2-[pentanoyl[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]amino]butanoic Acid (Valsartan (R)-Enantiomer);Tox21_111447;BDBM50282371;SC1407;AKOS015854410;AKOS026751459;CS-O-08393;VALSARTAN IMPURITY A [EP IMPURITY];CAS-137862-53-4;CS-0011419;A807313;A886383;EN300-18528142;J-007070;Q27280672;N-pentanoyl-N-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-D-valine;(2R)-3-Methyl-2-[pentanoyl[[2'(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]amino]butanoic Acid;(R)-[N-VALERYL-N-([2'-(1H-TETRAZOLE-5-YL)BIPHEN-4-YL]METHYL)VALINE);(2R)-3-METHYL-2-(N-{[2'-(1H-1,2,3,4-TETRAZOL-5-YL)-[1,1'-BIPHENYL]-4-YL]METHYL}PENTANAMIDO)BUTANOIC ACID;(2R)-3-methyl-2-[1-oxopentyl-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]amino]butanoic acid;(2R)-3-methyl-2-[pentanoyl-[[4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl]methyl]amino]butanoic acid;(R)-2-(N-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)pentanamido)-3-methylbutanoicacid;(R)-3-Methyl-2-{pentanoyl-[2''-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amino}-butyric acid

Chemical Property of (R)-2-(N-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)pentanamido)-3-methylbutanoic acid

Chemical Property:

• Vapor Pressure: 1.06E-19mmHg at 25°C
• Melting Point: 108-110°C
• Boiling Point: 684.9°C at 760 mmHg
• PKA: 3.56±0.10(Predicted)
• Flash Point: 368°C
• PSA: 112.07000
• Density: 1.212g/cm³
• LogP: 4.16170
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 435.22703980
• Heavy Atom Count: 32
• Complexity: 608

Purity/Quality:

99%, ^*data from raw suppliers

ent-Valsartan ^*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=C2C3=NNN=N3)C(C(C)C)C(=O)O
• Isomeric SMILES: CCCCC(=O)N(CC1=CC=C(C=C1)C2=CC=CC=C2C3=NNN=N3)[C@H](C(C)C)C(=O)O
• Uses: ent-Valsartan is the (R)-enantiomer of Valsartan ent-Valsartan (Valsartan USP Related Compound A) is the (R)-enantiomer of Valsartan (V095750).

Technology Process of (R)-2-(N-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)pentanamido)-3-methylbutanoic acid

There total 112 articles about (R)-2-(N-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)pentanamido)-3-methylbutanoic 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: 99.9%

(S)-N-(1-carboxy-2-methyl-prop-1-yl)-N-pentarloyl-N-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl-methyl]amine barium salt → N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine (137862-53-4,137862-87-4)

Guidance literature:

With hydrogenchloride; water; pH=2 - 2.5;

Reference yield: 95.0%

N-[[2'-(1-triphenylmethyltetrazol-5yl)biphenyl-4-yl]methyl]-N-valeryl-L-valine methyl ester (781664-81-1) → N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine (137862-53-4,137862-87-4)

Guidance literature:

N-[[2'-(1-triphenylmethyltetrazol-5yl)biphenyl-4-yl]methyl]-N-valeryl-L-valine methyl ester; With methanol; potassium hydroxide; for 4h; Heating / reflux;

With water; for 5h; Heating / reflux;

Reference yield: 92.0%

(2S)-3-methyl-2-{N-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-N'-(thiophene-2-carbonyl)-amino}-butanoic acid (1033772-60-9) → N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine (137862-53-4,137862-87-4)

Guidance literature:

With sodium azide; dichloro[(-)-sparteine-N,N']copper(II); In ethyl acetate; at 70 - 80 ℃; for 4h; Concentration; Reagent/catalyst; Large scale;

upstream raw materials:

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

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

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

C₁₆H₁₃O₂N

Downstream raw materials:

(S)-2-((S)-2-(N-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)pentanamido)-3-methylbutanamido)-3-phenylpropanoic acid

6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide

(S)-N-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-N-(3-methyl-1-morpholino-1-oxobutan-2-yl)pentanamide

Refernces

• 1、 -. "Valsartan without genotoxic impurity and preparation method thereof (by machine translation)". . . Retrieved 2020/05/09.
• 2、 -. "Method for treating azide ions, non-genotoxic impurity Sartan raw material medicine and immediate thereof". Paragraph 0105. . Retrieved 2019/05/28.