Ammonium Acetate → tert-Butyl [(2S,3S)-2-methyl-4-oxoazetidin-3-yl]carbamate

Participants

Reaction Steps

A solution of 4.98 g of (3S-trans)-3-t-butoxycarbonylamino-1-hydroxy-4-methylazetidinone in 200 ml of methanol was treated with 132 ml of 4.5 M ammonium acetate and then 66 ml of 1.5 titanium trichloride and stirred for 4.5 hours. The aqueous solution was diluted with an equal volume of 8% sodium chloride and extracted with ethyl acetate to give 3.48 g of crude product. Recrystallization from ether-hexane yielded 3.3 g of the title compound.

Provenance & Evidence