Methyl valinate hydrochloride → HCID 67409233, compound

HRID 453945Notes

Reaction equation

HRID 453945 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@H:5]([CH:7]([CH3:9])[CH3:8])[NH2:6].Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]#[N:26])=[CH:15][CH:14]=1>>[CH3:2][O:3][C:4](=[O:10])[C@H:5]([CH:7]([CH2:9][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]#[N:26])=[CH:17][CH:18]=1)[CH3:8])[NH2:6]

Participants

3

Reactant 2

HCID 111190Methyl valinate hydrochlorideHCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

Product 1

HCID 67409233HCID 67409233, compound

Procedure

L-valine methyl ester hydrochloride is N-alkylated with 4-bromomethyl-2′-cyanobiphenyl, the product 4-[(2′-cyanobiphenyl-4-yl)methyl]-(L)-valine methyl ester thus formed is N-acylated with valeryl chloride to give N-[(2′-cyanobiphenyl-4-yl)methyl]-N-valeryl-(L)-valine methyl ester. N-[(2′-cyanobiphenyl-4-yl)methyl]-N-valeryl-(L)-valine methyl ester is treated with tributyltin azide to give valsartan methyl ester, which is then hydrolyzed under alkaline condition to give finally valsartan.

Sources & evidence

ORD record
ord-3122c9e80b454d229b006298fc003270
Source dataset
uspto-grants-2013_07
Patent number
US08492577B2

Reaction notes

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