N-[(4-Bromophenyl)methyl]-N-(1-oxopentyl)-L-valine → HCID 178447302, compound

HRID 453948Notes

Reaction equation

HRID 453948 reaction equation
Br[C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]([C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH3:19])[C@H:8]([C:12]([OH:14])=[O:13])[CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[NH:23]1[C:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2B(O)O)=[N:26][N:25]=[N:24]1>>[CH3:19][CH2:18][CH2:17][CH2:16][C:15]([N:7]([C@H:8]([C:12]([OH:14])=[O:13])[CH:9]([CH3:11])[CH3:10])[CH2:6][C:5]1[CH:4]=[CH:3][C:2]([C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:27]2[NH:23][N:24]=[N:25][N:26]=2)=[CH:22][CH:21]=1)=[O:20]

Participants

3

Reactant 2

HCID 11696368N-[(4-Bromophenyl)methyl]-N-(1-oxopentyl)-L-valineHCID 178514830HCID 178514830, compound

Product 1

HCID 178447302HCID 178447302, compound

Procedure

WO 2005/102987 provides the reaction of 4-Bromobenzylic bromide and hydrochloride methylester of L-valine methylester in an aprotic solvent and organic or an inorganic base to give methylester of N-(4-bromobenzyl)-L-valine which is deprotected to give N-(4-bromobenzyl)-L-valine. This on acylation with valeryl chloride yields N-(4-bromobenzyl)-N-valeryl-L-valine. Valsartan is prepared by the reaction of N-(4-bromobenzyl)-N-valeryl-L-valine and 2-(1H-tetrazole-5-yl)phenylboronic acid in palladiumtetrakistriphenylphosphine.

Sources & evidence

ORD record
ord-34e4985928a841238585a60b1f06dfe5
Source dataset
uspto-grants-2013_07
Patent number
US08492577B2

Reaction notes

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