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Process for the preparation of (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid

IP.com Disclosure Number: IPCOM000244802D
Publication Date: 2016-Jan-17
Document File: 1 page(s) / 171K

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Process for the preparation of (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-

butoxycarbonyl)amino)-2-methylpentanoic acid

(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid, referred to herein as compound 1, may be an intermediate in the preparation of 4-{[(2S,4R)- 1-(4-Biphenylyl)-5-ethoxy-4-methyl-5-oxo-2-pentanyl]amino}-4-oxobutanoic acid (referred to as compound A).

Compound 1 was prepared from (2R,4S)-5-(4-bromophenyl)-4-((tert-butoxycarbonyl)amino)- 2-methylpentanoic acid by Suzuki coupling with phenylboronic acid by employing the process discussed in the literature (J. AM. CHEM. SOC. 2009, 131, 16346-16347).

The compound 1 was obtained in high purity and yield which may be further adapted by process optimization.

The obtained compound 1 can be converted to compound A by process described in the literature, for example US8946481.