Triethylamine → N-((2'-Cyano(1,1'-biphenyl)-4-yl)methyl)-N-(1-oxopentyl)-L-valine methyl ester

HRID 1443313Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1443313
[CH3:1][CH2:2][CH2:3][CH2:4][C:5]([N:7]([C@H:26]([C:30]([OH:32])=[O:31])[CH:27]([CH3:29])[CH3:28])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=2[C:21]2[NH:22]N=NN=2)=[CH:13][CH:14]=1)=[O:6].[CH3:33]OC(=O)[C@H](C(C)C)NCC1C=CC(C2C=CC=CC=2C#N)=CC=1.C(Cl)(=O)CCCC.C(N(CC)CC)C>ClCCl>[CH3:33][O:32][C:30](=[O:31])[C@H:26]([CH:27]([CH3:28])[CH3:29])[N:7]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=2[C:21]#[N:22])=[CH:11][CH:10]=1)[C:5](=[O:6])[CH2:4][CH2:3][CH2:2][CH3:1]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 16744794N-((2'-Cyano(1,1'-biphenyl)-4-yl)methyl)-L-valine methyl esterHCID 178447302HCID 178447302, Verbindung

Produkt 1

HCID 16744795N-((2'-Cyano(1,1'-biphenyl)-4-yl)methyl)-N-(1-oxopentyl)-L-valine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Briefly, the process for the preparation of valsartan comprises of the condensation of N-[(2′-cyanobiphenyl-4-yl)methyl]-(L)-valine methyl ester of Formula II with valeryl chloride of Formula III in the presence of triethylamine and dichloromethane, followed by flash chromatography, to give the compound N-[(2′-cyanobiphenyl-4-yl)methyl]-N-valeryl-(L)-valine methyl ester of Formula IV. The compound of Formula IV on tetrazole formation using tributyltin azide and subsequent hydrolysis using sodium hydroxide, followed by flash chromatography, gives valsartan of Formula I.

Quellen und Nachweise

ORD-Eintrag
ord-cc81514b625a4b96bffa630fcbe18e96
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659406B2

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