Convenient Method for Synthesis of N-Protected r-Amino Epoxides : Key Intermediates for HIV Protease Inhibitors

  • Blacker A
  • Roy M
  • Hariharan S
 et al. 
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Abstract

ABSTRACT: A convenient method for synthesis of 2R,3S and 2S,3S N-Boc phenylalanine epoxides using readily available allylamine is described. Previous methods employed multistep synthetic routes from L-phenyl alanine that include use of m- chloroperbenzoic acid (m-CPBA) and a chromatographic method for purification of the desired diastereomers. Column purification could be eliminated by bringing in much improvement in the existing process. The process was further enhanced by replacing m- CPBA with oxone, an ecofriendly reagent advantageous for commercial application. The overall green process discussed involves the recovery and recycling of enantiomers of chiral allyl amines and judicial separation of diastereomers of the epoxides using simple economical methods.

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Authors

  • A John Blacker

  • Mita Roy

  • Sivaramkrishanan Hariharan

  • Catherine Headley

  • Abhay Upare

  • Ashutosh Jagtap

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