Sodium Chloride → HCID 13219837, compound

Participants

Reaction Steps

To a solution of 3.28 g of (3S, 4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-4-[(phenylthio)ethynyl]-2-azetidinone in 75.0 ml of anhydrous methylene chloride were added, under an atmosphere of nitrogen gas, 3.5 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 1.14 g of sodium bicarbonate, 75 ml of water and 300 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 then 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 3:1 by volume mixture of cyclohexane and ethyl acetate, to give 3.09 g (yield 89.9%) of the title thioester compound, melting at 94°-95° C.

Provenance & Evidence