Valeryl chloride → Valeryl chloride

HRID 453949Notes

Reaction equation

HRID 453949 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH:21]([CH3:23])[CH3:22])[NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]#[N:20])=[CH:9][CH:8]=1.[C:25]([Cl:31])(=[O:30])[CH2:26][CH2:27][CH2:28][CH3:29]>>[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH:21]([CH3:22])[CH3:23])[N:5]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]#[N:20])=[CH:9][CH:8]=1)[C:25](=[O:30])[CH2:26][CH2:27][CH2:28][CH3:29].[C:25]([Cl:31])(=[O:30])[CH2:26][CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 61186Valeryl chlorideHCID 16744794N-((2'-Cyano(1,1'-biphenyl)-4-yl)methyl)-L-valine methyl ester

Product 2

HCID 61186Valeryl chlorideHCID 16744795N-((2'-Cyano(1,1'-biphenyl)-4-yl)methyl)-N-(1-oxopentyl)-L-valine methyl ester

Procedure

According to US 2006/0149079 A1 N-[(2′-cyanobiphenyl-4-yl)methyl]-(L)-valine methylester is acylated with valerylchloride in the presence of inorganic base to give N-[(2′-cyanobiphenyl-4-yl)methyl]-N-valeryl-(L)-valine methylester with valerylchloride, followed by the conversion of cyano to tetrazole and hydrolyzing the tetrazole derivative to obtain valsartan.

Sources & evidence

ORD record
ord-8a943008a0814b1da97cc487f2d9b617
Source dataset
uspto-grants-2013_07
Patent number
US08492577B2

Reaction notes

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