Sodium Sulfite → HCID 10870082, compound

Participants

Reaction Conditions

Reaction Steps

In 16 ml of dry dichloromethane is dissolved 0.50 g of (3S,4S)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-azetidinone obtained in Example 37 and, on cooling at -15° C., 0.368 g of chlorosulfonyl isocyanate is added, followed by stirring for 30 minutes. A 15-ml aqueous solution of 0.72 g of sodium sulfite is added and the solution is warmed to room temperature, followed by stirring for 1 hour. The dichloromethane is distilled off under reduced pressure and the residue is extracted twice with ethyl acetate-tetrahydrofuran (3:1, v/v). The extract is washed with aqueous sodium chloride, dried over mangesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography [eluent: chloroform-ethyl acetate-methanol (40:55:5, v/v/v)] to give 0.323 g of (3S,4S)-3-benzyloxycarbonylamino-4-carbamoyloxymethyl-2-azetidinone.

Provenance & Evidence