One-pot efficient synthesis of N(α)-urethane-protected β- and γ-amino acids

Marta Cal; Mariusz Jaremko; Łukasz Jaremko; Piotr Stefanowicz

doi:10.1007/s00726-012-1443-3

One-pot efficient synthesis of N(α)-urethane-protected β- and γ-amino acids

Amino Acids. 2013 Mar;44(3):1085-91. doi: 10.1007/s00726-012-1443-3. Epub 2012 Dec 19.

Authors

Marta Cal¹, Mariusz Jaremko, Łukasz Jaremko, Piotr Stefanowicz

Affiliation

¹ Faculty of Chemistry, University of Wrocław, ul. F. Joliot-Curie 14, Wroclaw, Poland.

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.

Publication types

Evaluation Study
Research Support, Non-U.S. Gov't

MeSH terms

Chemistry Techniques, Synthetic / methods*
Molecular Structure
Urethane / chemistry*
beta-Alanine / chemical synthesis*
beta-Alanine / chemistry
gamma-Aminobutyric Acid / chemical synthesis
gamma-Aminobutyric Acid / chemistry

Substances

beta-Alanine
Urethane
gamma-Aminobutyric Acid