Kinetic Resolution of Piperazine-2-Carboxamide by Leucine Aminopeptidase. An Application in the Synthesis of the Nucleoside Transport Blocker (-) Draflazine

M. A. Bruce Bristol-Myers Squibb Pharmaceutical Research Institute, Wallingford, Connecticut, 06492-7660, USA

D. R. St. Laurent Bristol-Myers Squibb Pharmaceutical Research Institute, Wallingford, Connecticut, 06492-7660, USA

G. S. Poindexter Bristol-Myers Squibb Pharmaceutical Research Institute, Wallingford, Connecticut, 06492-7660, USA

I. Monkovic Bristol-Myers Squibb Pharmaceutical Research Institute, Wallingford, Connecticut, 06492-7660, USA

S. Huang Bristol-Myers Squibb Pharmaceutical Research Institute, Wallingford, Connecticut, 06492-7660, USA

N. Balasubramanian Bristol-Myers Squibb Pharmaceutical Research Institute, Wallingford, Connecticut, 06492-7660, USA

Abstract

The resolution of N-t-Boc-piperazine carboxamide 5 proceeded smoothly in the presence of leucine aminopeptidase to produce acid (S)-1 and amide (R)-5 with good optical purity. Sequential alkylation and functional group manipulation of carboxamide (S)-5 provided the known nucleoside transport blocker draflazine (-) 2.

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Kinetic Resolution of Piperazine-2-Carboxamide by Leucine Aminopeptidase. An Application in the Synthesis of the Nucleoside Transport Blocker (-) Draflazine

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Kinetic Resolution of Piperazine-2-Carboxamide by Leucine Aminopeptidase. An Application in the Synthesis of the Nucleoside Transport Blocker (-) Draflazine

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