One-pot efficient synthesis of N α-urethane-protected β- And γ-amino acids

Marta Cal, Mariusz Jaremko*, Łukasz Jaremko, Piotr Stefanowicz

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

1-[(4-Methylphenyl)oxy]pyrrolidine-2,5-dione and 1-[(4-methylphenyl)oxy] piperidine-2,6-dione react in a Lossen-type reaction with primary alcohols in the presence of triethylamine to furnish corresponding N α- urethane-protected β-alanine and γ-aminopropionic acid (GABA), respectively, with excellent yields and purities, in an essentially "one-pot" procedure.

Original languageEnglish (US)
Pages (from-to)1085-1091
Number of pages7
JournalAmino Acids
Volume44
Issue number3
DOIs
StatePublished - Mar 2013
Externally publishedYes

Keywords

  • β- and γ-Amino acids
  • β-Alanine
  • Anthranilic acid
  • CBz
  • GABA
  • Lossen rearrangement
  • N -Urethane-protection
  • N-Hydroxyimides

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Organic Chemistry

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