| Identification | Back Directory | [Name]
(2S,4S)-3-BENZOYL-2-T-BUTYL-4-METHYL-1,3-OXAZOLIDIN-5-ONE | [CAS]
104057-64-9 | [Synonyms]
(2S,4S)-3-BENZOYL-2-T-BUTYL-4-METHYL-1,3-OXAZOLIDIN-5-ONE
3-BENZOYL-2-2(1,1-DIMETHYLETHYL)-4-METHYL-5-OXAZOLIDINONE
(2S,4S)-3-Benzoyl-2-(tert-butyl)-4-methyloxazolidin-5-one
5-Oxazolidinone, 3-benzoyl-2-(1,1-dimethylethyl)-4-methyl-, (2S,4S)- | [Molecular Formula]
C15H19NO3 | [MDL Number]
MFCD01318296 | [MOL File]
104057-64-9.mol | [Molecular Weight]
261.32 |
| Hazard Information | Back Directory | [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.
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