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

Andrew B. Hughes; Brad E. Sleebs

doi:10.1071/CH05199

RESEARCH ARTICLE

Previous Next Contents Vol 58(11)

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

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

+ Author Affiliations

- Author Affiliations

^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

Australian Journal of Chemistry 58(11) 778-784 https://doi.org/10.1071/CH05199
Submitted: 10 August 2005 Accepted: 20 September 2005 Published: 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.

Acknowledgment

We thank La Trobe University for the provision of a Post-Graduate Scholarship awarded to B.E.S.

References

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

Abstract

Acknowledgment

Subscriber Login