Synthesis and Explosion Hazards of 4-Azido-l-phenylalanine

J Org Chem. 2018 Apr 20;83(8):4525-4536. doi: 10.1021/acs.joc.8b00270. Epub 2018 Apr 2.

Abstract

A reliable, scalable, cost-effective, and chromatography-free synthesis of 4-azido-l-phenylalanine beginning from l-phenylalanine is described. Investigations into the safety of the synthesis reveal that the Ullman-like Cu(I)-catalyzed azidation step does not represent a significant risk. The isolated 4-azido-l-phenylalanine product, however, exhibits previously undocumented explosive characteristics.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides / chemical synthesis*
  • Azides / chemistry
  • Catalysis
  • Copper / chemistry
  • Molecular Structure
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / chemical synthesis
  • Phenylalanine / chemistry

Substances

  • Azides
  • 4-azidophenylalanine
  • Phenylalanine
  • Copper