Synthesis of New β-Amino Acids via 5-Oxazolidinones and the Arndt–Eistert Procedure

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Contents Vol 58(11)

doi:10.1071/CH05199

Synthesis of New β-Amino Acids via 5-Oxazolidinones and the Arndt–Eistert Procedure

Andrew B. Hughes ^A ^C, Brad E. Sleebs ^B

^A Department of Chemistry, La Trobe University, Melbourne VIC 3086, Australia.
^B Walter and Eliza Hall Institute of Medical Research, Melbourne VIC 3086, Australia.
^C Corresponding author. Email: a.hughes@latrobe.edu.au





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Australian Journal of Chemistry 58(11) 778–784 http://dx.doi.org/10.1071/CH05199
Submitted: 10 August 2005 Accepted: 20 September 2005 Published online: 9 December 2005

Abstract

N-Methyl β-amino acids are potentially useful amino acid derivatives for incorporation in lead peptide therapeutics. The syntheses of five such compounds are presented. Their synthesis via 6-oxazinanones was low yielding. Alternatively, reductive cleavage of a 5-oxazolidinone gave the N-methyl α-amino acid, which was then homologated via an Arndt–Eistert procedure in high yield to give the N-methyl β-amino acid.