Acetic Acid → (3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-(2-hydroxy-1-phenylethoxy)-azetidin-2-one

Participants

Reaction Steps

A THF solution of 1 N BU4NF (0.84 ml, 0.84 mmole) containing AcOH (35 mg, 0.56 mmole) was added to a solution of (3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-{2-(tert-butyldimethylsilyl)oxy-1-phenylethoxy}-azetidin-2-one (430 mg, 0.70 mmole) in THF (5 ml) at 0-5° C. The mixture was stirred at room temperature for 3 hrs, then poured into a silica gel column. The column was eluented with methanol-ethyl acetate (5:95) and 260 mg of (3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-(2-hydroxy-1-phenylethoxy)-azetidin-2-one was obtained (74% yield).

Provenance & Evidence