Pyridine → (3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-{2-(p-toluenesulfonyl)oxy-1-phenylethoxy}-azetidin-2-one

Participants

Reaction Conditions

Reaction Steps

p-Toluenesulfonyl chloride (119 mg, 0.62 mmol) was added to an ice-cooled solution of (3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-(2-hydroxy-1-phenylethoxy)-azetidin-2-one (260 mg, 0.52 mmol) and pyridine (493 mg, 6.2 mmol) in dichloromethane (7 ml). The mixture was stirred at 0° C. for 2 hrs and then at room temperature overnight. After removal of solvent, the residue was purified by silica gel column chromatography using ethyl acetate-hexane (8:3) as eluent and 160 mg of (3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-{2-(p-toluenesulfonyl)oxy-1-phenylethoxy}-azetidin-2-one was obtained (47% yield).

Provenance & Evidence