L-Valine → (S)-2-(4-bromobenzyl)amino-3-methylbutyric acid

HRID 453952Notes

Reaction equation

[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH2:10][C@H:11]([C:15]([OH:17])=[O:16])[CH:12]([CH3:14])[CH3:13].[BH4-].[Na+]>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:10][C@@H:11]([CH:12]([CH3:14])[CH3:13])[C:15]([OH:17])=[O:16])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 6287L-Valine

HCID 707414-Bromobenzaldehyde

HCID 4311764Sodium borohydride

Product 1

HCID 11673643(S)-2-(4-bromobenzyl)amino-3-methylbutyric acid

Procedure

EP 1777224 describes the condensation of p-Bromobenzaldehyde with L-valine followed by reduction with sodium borohydride to give (S)-2-(4-bromobenzyl)amino-3-methylbutyric acid. (S)-2-(4-bromobenzyl)amino-3-methyl butyric acid is treated with valerylchloride to give (S)-2-(4-bromobenzyl)-pentanoyl-amino-3-methyl butyric acid. (S)-2-(4-bromobenzyl)-pentanoyl-amino-3-methyl butyric acid is treated with 2-(2H-tetrazol-5-yl)benzene-boronic acid in tetrahydrofuran, triphenylphosphine and palladiumacetate yield valsartan.

Sources & evidence

ORD record: ord-bf95eb48b17c4bbcbde3cdafe6d0b497
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492577B2

Reaction notes

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