A practical approach to the synthesis of 2,4-disubstituted oxazoles from amino acids.
[reaction: see text] A new sequence for the synthesis of various 2,4-disubstituted oxazoles from alpha-amino acids is reported. The method is shown to be general and incorporates the reagent combination, triphenylphosphine/hexachloroethane, for cyclodehydration of intermediate alpha-acylamino aldehydes. Implementation of this reagent system for the conversion of alpha-acylamino ketones to oxazoles is briefly investigated.
Morwick
Tina
T
Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, Connecticut 06877-0368, USA. tmorwick@rdg.boehringer-ingleheim.com
Hrapchak
Matt
M
DeTuri
Molly
M
Campbell
Scot
S
D000596:Amino Acids / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010080:Oxazoles / Q000138:chemical synthesis*
D000596:Amino Acids; D010080:Oxazoles