Synthesis and Explosion Hazards of 4-Azido-l-phenylalanine.
- Author(s): Richardson, Mark B
- Brown, Derek B
- Vasquez, Carlos A
- Ziller, Joseph W
- Johnston, Kevin M
- Weiss, Gregory A
- et al.
Published Web Locationhttps://doi.org/10.1021/acs.joc.8b00270
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.