Der Pharma Chemica
Journal for Medicinal Chemistry, Pharmaceutical Chemistry, Pharmaceutical Sciences and Computational Chemistry

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Abstract

Alternative synthesis of Valsartan via Negishi coupling

Author(s): Srinivas Ambati, Hanumantha Rao Penikelapati, T V Maruthikumar, Narahari Babu Ambati

A highly efficient approach to the synthesis of valsartan is described. Directed ortho-metalation of 4,4-dimethyl-2-phenyl-4,5-dihydrooxazole provides the key organozinc intermediate for palladium catalysed biaryl coupling with methyl N-(4-bromobenzyl)-N-pentanoyl-L-valinate (aryl bromide) obtained from alkylation of methyl N–pentanoyl-L-valinate. This methodology overcomes many of drawbacks associated with previously reported syntheses.


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