Sodium Chloride → HCID 13219844, compound

Participants

Reaction Steps

To a solution of 718 mg of (3S, 4S)-3-[(R)-1-hydroxyethyl]-4-[(phenylthio)ethynyl]-2-azetidinone in 8 ml of anhydrous methylene chloride was added, under an atmosphere of nitrogen gas, 1.1 ml of trifluoroacetic acid, with stirring and ice-cooling. The mixture was then stirred for 30 minutes under ice-cooling and for a further 1.5 hours at room temperature. The reaction mixture was then poured into a mixture of 2.44 g of sodium bicarbonate, 15 ml of water and 30 ml of ethyl acetate. The mixture was saturated with sodium chloride and the organic layer was separated. The aqueous layer was extracted twice with ethyl acetate. The organic layer and the ethyl acetate extracts were combined, and the combined solution was washed successively with an aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulphate. The solvent was distilled off under reduced pressure and the residue was subjected to column chromatography through silica gel, eluted with a 1:3 by volume mixture of cyclohexane and ethyl acetate, to give 281 mg (yield 36.5%) of the title thioester compound, which was recrystallized from a mixture of ethyl acetate and hexane to give crystals melting at 121.5-123.5° C.

Provenance & Evidence