An expedient route to the tetrazole analogues of alpha-amino acids.
[reaction: see text] Convenient conditions are described for the transformation of alpha-aminonitriles to the tetrazole analogues of alpha-amino acids. Refluxing the starting material in water/2-propanol at 80 degrees C with sodium azide and catalytic zinc bromide affords the tetrazole product in yields generally exceeding 90%.
Department of Chemistry and The Skaggs Institute of Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Zachary P
ZP
Demko
K Barry
KB
Sharpless
D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D002626:Chemistry, Pharmaceutical; D009570:Nitriles / Q000737:chemistry; D019810:Sodium Azide / Q000737:chemistry; D013777:Tetrazoles / Q000138:chemical synthesis*; D015032:Zinc
D000596:Amino Acids; D009570:Nitriles; D013777:Tetrazoles; D019810:Sodium Azide; D015032:Zinc