Hydrochloric Acid → HCID 56611618, compound

Participants

Reaction Steps

In 12 ml of dichloromethane is dissolved 1.06 g of (3S,4S)-4-cyano-3-triphenylmethylamino-2-azetidinone and, following addition of 1.02 g of tetra-n-butylammonium hydrogen sulfate, 0.68 ml of 30% aqueous hydrogen peroxide and 4.5 ml of 1 N sodium hydroxide are added under ice-cooling and stirring. The mixture is stirred vigorously for 50 minutes and poured into ice water containing 1.3 ml of 1 N hydrochloric acid. After phase separation, the aqueous layer is extracted twice with chloroform. The organic layers are combined and washed with an aqueous solution of sodium thiosulfate and sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The residue is chromatographed on a silica gel column [eluant: chloroform-ethyl acetate-methanol (50:50:5)] to give 0.223 g of (3S,4S)-4-carbamoyl-3-triphenylmethylamino-2-azetidinone.

Provenance & Evidence