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

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 purifica...

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Published inOrganic process research & development Vol. 15; no. 2; pp. 331 - 338
Main Authors Blacker, A. John, Roy, Mita, Hariharan, Sivaramkrishanan, Headley, Catherine, Upare, Abhay, Jagtap, Ashutosh, Wankhede, Karuna, Mishra, Sushil Kumar, Dube, Dagadu, Bhise, Sanjay, Vishwasrao, Sandesh, Kadam, Nitin
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 01.03.2011
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
BUILDING-BLOCK
EPOXIDATION
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Summary: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.
ISSN:1083-6160
1520-586X
DOI:10.1021/op100174