Uses
(2S,4S)-3-Benzoyl-2-t-butyl-4-methyl-1,3-oxazolidin-5-one is used as a reagent for the preparation of enantiopure α-methyl-α-aminocarboxylic acids; precursor to the 4-methylidene derivative; a radicalophile; a Michael acceptor; and an ene component for Diels-Alder additions, with formation of more complex α-amino acids.
Preparation
(2S,4S)-3-BENZOYL-2-T-BUTYL-4-METHYL-1,3-OXAZOLIDIN-5-ONE is synthesized by: the sodium salt of the pivalaldehyde imine of (S)-alanine is cyclized to the oxazolidinone by reaction with PhCOCl in CH2Cl2 at low temperature; the cis/trans ratio in the crude product depends upon the exact reaction conditions, it is usually 4:1; purification by a combination of crystallization and chromatography gives the pure cis derivative in 60-70% yield.
storage
(2S,4S)-3-Benzoyl-2-t-butyl-4-methyl-1,3-oxazolidin-5-one is stable for years when stored in a bottle.
