An Improved Synthesis of the New Angiotensin Converting Enzyme Inhibitor CV-5975 via a Chemoenzymatic Process(Organic,Chemical)

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A chemoenzymatic synthesis of the new angiotensin converting enzyme inhibitor CV-5975 (1) is described. The optically active key intermediate for the synthesis of 1, ethyl (R-6-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxyhexanoate ((R)-4), was prepared by kinetic resolution of the racemic α-hydroxyester ((RS)-4) with a lipase and also by asymmetric reduction of the α-oxoester (3) with baker's yeast, The enantiomeric excess (ee) of the a-hydroxyester ((R)-4) produced by these enzymatic procedures exceeded 60%. This optically active alcohol ((R)-4) was converted to its mesylate ((R)-5), which was then subjected to S_N2 reaction with the aminobenzothiazepine derivative (2) followed by deprotection to yield 1.

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