A New General and Facile Method for the Synthesis of 4-Alkyl-1,3-oxazoline-4-carboxylic Acids from N-Acyl-2-alkylserines

Sebastian Olczyk; Janina E. Kamińska; Beata Kolesińska; Zbigniew J. Kamiński

doi:10.1055/s-2007-983708

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Synthesis 2007(12): 1807-1810
DOI: 10.1055/s-2007-983708

PAPER

A New General and Facile Method for the Synthesis of 4-Alkyl-1,3-oxazoline-4-carboxylic Acids from N-Acyl-2-alkylserines

Sebastian Olczyk^a, Janina E. Kamińska*^a, Beata Kolesińska^b, Zbigniew J. Kamiński^b
^a Institute of General Food Chemistry, Technical University of ŁódŸ, ul. B. Stefanowskiego 4/10, 90-924 ŁódŸ, Poland
Fax: +48(42)6362860; e-Mail: janina.kaminska@p.lodz.pl;
^b Institute of Organic Chemistry, Technical University of ŁódŸ, ul. S. ¯eromskiego 116, 90-924 ŁódŸ, Poland

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Publication History

Received 12 February 2007
Publication Date:
08 June 2007 (online)

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Abstract

A new synthesis of 4-alkyl-1,3-oxazoline-4-carboxylic acids involves the thermal rearrangement of 4-alkyl-4-hydroxymethyl-1,3-oxazolin-5-ones prepared from N-acyl-2-alkylserines or N-protected peptides with a C-terminal 2-alkylserine residue. The rearrangement is fast and affords HPLC pure title compounds in 68-96% yield both from racemic and enantiomerically pure N-acyl-2-alkyl serines as well as from respective peptides.

Key words

2-alkylserines - heterocycles - rearrangement

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