Methanol → HCID 11139540, compound

Participants

Reaction Conditions

Reaction Steps

In a mixture of 80 ml of methanol and 16 ml of dichloromethane is dissolved 0.8 g of (3S,4R)-3-benzyloxycarbonylamino-4-styryl-2-azetidinone obtained in Example 33 and, with cooling at -78° C., ozone gas is bubbled into the solution for 30 minutes. Thereafter, the excess ozone is purged with nitrogen and 0.19 g of sodium borohydride is added, followed by warming the solution to about 0° C. and stirring with ice-cooling for 30 minutes. To the mixture is added 0.3 g of acetic acid and the resulting mixture is concentrated under reduced pressure. To the residue are added ethyl acetate and water, and the ethyl acetate layer is separated. The aqueous layer is extracted with ethyl acetate and the combined ethyl acetate layer is washed with aqueous sodium chloride, dried over mangesium sulfate and concentrated under reduced pressure. The residue is crystallized from diethyl ether and the crystals are collected by filtration to give 0.5 g of (3S,4S)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-azetidinone.

Provenance & Evidence