Ethyl Acetate → HCID 56617225, compound

Participants

Reaction Steps

With stirring at room temperature, a solution of 0.467 g of (3S,4R)-1-[(1R)-1,2-di(methoxycarbonyl)ethyl]-3-benzyloxycarbonylamino-4-styryl-2-azetidinone in 20 ml of ethyl acetate and 0.068 g of n-Bu4NHSO4 are added to a solution of 0.79 g of potassium permanganate in 20 ml of water, and the mixture is stirred at room temperature for 2 hours. To the reaction mixture is added an aqueous solution of sodium thiosulfate and the mixture is passed through a Celite layer and washed with water and ethyl acetate. The aqueous layer is separated, adjusted to pH 1.5 with 5N hydrochloric acid and extracted twice with ethyl acetate. The extract is washed with aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is purified by silica gel column chromatography [eluent: ethyl acetate-n-hexane (1:1 to 2:1, v/v)] to give 0.205 g of (3S,4R)-1-[(1R)-1,2 -di(methoxycarbonyl)ethyl]-3-benzyloxycarbonylamino-4-methoxycarbonyl-2-azetidinone and 23 mg of (3S,4R)-3-benzyloxycarbonylamino-4-methoxycarbonyl-2-azetidinone.

Provenance & Evidence