4'-(Bromomethyl)-2-cyanobiphenyl → 4-[(2'-cyanobiphenyl-4-yl)methyl]-(L)-valine benzyl ester

HRID 901309Notes

Reaction equation

HRID 901309 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:16])[C@H:11]([CH:13]([CH3:15])[CH3:14])[NH2:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]#[N:32])=[CH:21][CH:20]=1>>[CH2:2]([O:9][C:10](=[O:16])[C@H:11]([CH:13]([CH2:14][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]#[N:32])=[CH:23][CH:24]=1)[CH3:15])[NH2:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 11601206L-Valine benzyl ester hydrochloride

Product 1

HCID 674085734-[(2'-cyanobiphenyl-4-yl)methyl]-(L)-valine benzyl ester

Procedure

L-valine benzyl ester hydrochoride is N-alkylated with 4-bromomethyl-2′-cyanobiphenyl, the product 4-[(2′-cyanobiphenyl-4-yl)methyl]-(L)-valine benzyl ester so formed is N-acylated with valeryl chloride to give N-[(2′-cyanobiphenyl-4-yl)methyl]-N-valeryl-(L)-valine benzyl ester. N-[(2′-cyanobiphenyl-4-yl)methyl]-N-valeryl-(L)-valine benzyl ester is treated with tributyltin azide to give valsartan benzyl ester. Valsartan benzyl ester is subjected to catalytic hydrogenation using for example palladium-charcoal as catalyst to give valsartan.

Sources & evidence

ORD record
ord-d1b07386cb654bb890665724af349d3c
Source dataset
uspto-grants-2008_04
Patent number
US07361770B2

Reaction notes

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