Imidazole → HCID 54163843, compound

Participants

Reaction Steps

To a solution of 28 mg (0.07 mmol) of 1-benzyl-3-(1-benzyloxycarbonyloxyethyl)-4-(1-methoxycarbonylethenyl)-2-azetidinone dissolved in 2 ml of methanol, 5 mg of 5% palladium charcoal was added and the mixture was stirred under hydrogen atmosphere for a night. The reaction solution was filtered with selite and the filtrate was washed with ethyl acetate and concentrated. To the concentrate were added 1 ml of DMF, 20 mg (0.3 mmol) of imidazole and 45 mg (0.3 mmol) of t-butyldimethylsilylchloride and the mixture was stirred for a night. Ice water was added to the reaction solution and the resultant was extracted with ether, washed with a saturated solution of NaCl, dried with magnesium sulfate, concentrated and purified with 2 g of silica-gel column (hexane:ether 1:1) to give 22 mg of 1-benzyl-4-(1-methoxycarbonylethyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone (yield: 84%). Comparison with the NMR data showed α:β=1:1.

Provenance & Evidence