Sodium Sulfite → N-(6phenylhexyl)-4-benzylsulphinyl-2-oxoazetidin-1-yl acetamide

Participants

Reaction Steps

A solution of N-(6-phenylhexyl)-4-benzylthio-2-oxoazetidin-1-yl acetamide (18.0 g, 43.8 mmol) in dichloromethane (500 ml) was cooled to -70° C. and a solution of m-chloroperbenzoic acid (6.7 g, 43.8 mmol) in dichloromethane (500 ml) added dropwise with stirring over 60 min. After a further 3 h at -60° C., the reaction mixture was shaken with a mixture of saturated aqueous sodium sulphite and saturated sodium hydrogen carbonate. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated to a solid which was titurated with ether and filtered. Two recrystallisations from ethyl acetate gave (4R,SR/4S,SS) N-(6phenylhexyl)-4-benzylsulphinyl-2-oxoazetidin-1-yl acetamide (3.8 g, 20%) mp 138-140° C.

Provenance & Evidence