Facile Preparation of N-Tosyl-L-Phenylalanine Chloromethyl Ketone

Author(s): Bing-Lei Gao, Shu-Tao Ma, Zhao-Peng Liu.

Journal Name: Letters in Organic Chemistry

Volume 6 , Issue 8 , 2009

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Abstract:

A method for the facile preparation of N-tosyl-L-phenylalanine chloromethyl ketone was developed. LPhenylalanine was tosylated and converted to the activated ester of p-nitrophenol. Subsequent reaction with dimethylsulfoxonium methylide and treatment with lithium chloride and methanesulfonic acid afforded the α- chloroketone. This practical procedure avoided the use of toxic and explosive diazomethane.

Keywords: Serine protease inhibitors, α-chloroketone, N-tosyl-L-phenylalanine chloromethyl ketone, ylides, sulfur

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Article Details

VOLUME: 6
ISSUE: 8
Year: 2009
Page: [648 - 649]
Pages: 2
DOI: 10.2174/157017809790443005
Price: $58

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