Valsartan benzyl ester → HCID 178447302, compound

HRID 453947Notes

Reaction equation

HRID 453947 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][C:5]([N:7]([C@H:26]([C:30]([O:32]CC1C=CC=CC=1)=[O:31])[CH:27]([CH3:29])[CH3:28])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]([C:21]3[N:25]=[N:24][NH:23][N:22]=3)=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)=[O:6]>[Pd]>[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:23]=[N:24][N:25]=2)=[CH:13][CH:14]=1)=[O:6]

Participants

3

Reactant 1

HCID 11283894Valsartan benzyl ester

Product 1

HCID 178447302HCID 178447302, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

L-valine benzyl ester hydrochloride 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-21ada994a0404dfa8e0a84327c4e7bba
Source dataset
uspto-grants-2013_07
Patent number
US08492577B2

Reaction notes

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