Hydrochloric Acid → HCID 56611618, compound

Participants

Reaction Steps

In 2 ml of dichloromethane is dissolved 160 mg of (3S,4S)-4-cyano-3-triphenylmethylamino-2-azetidinone and, following addition of 154 mg of tetra-n-butylammonium hydrogen sulfate, 0.103 ml of 30% aqueous hydrogen peroxide and 0.68 ml of 1N sodium hydroxide are added under ice-cooling and stirring. The mixture is stirred vigorously for 30 minutes and poured into ice water containing 0.22 ml of 1N hydrochloric acid. After phase separation, the aqueous layer is extracted twice with chloroform. The organic layers are combined, washed with aqueous 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 75 mg of (3S,4S)-4-carbamoyl-3-triphenylmethylamino-2-azetidinone. The IR and NMR spectra of this compound are identical with those of the compound obtained in Example 17.

Provenance & Evidence