Hydroquinone → HCID 86747601, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 0.48 g of allyl 2-[(3S,4R)-4-(4-allyloxycarbonylamino-3-(N-allyloxycarbonylaminomethyl)-2-oxobutyl]-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-oxoazetidin-1-yl]-2-oxoacetate and 0.39 ml of triethyl phosphite in 2.4 ml of toluene was stirred at 90° C. for 10 hours. After ylid was identified by thin layer chromatography the temperature was raised to 130° C. and 42 mg of hydroquinone was added. After stirring for 4 hours at 130° C., the reaction mixture was cooled to room temperature and then ethyl acetate was added. The organic layer was washed in turn with 5% aqueous potassium carbonate and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed on silica gel to give 0.28 g of allyl (5R,6S)-3-[2-allyloxycarbonylamino-1-(N-allyloxycarbonylaminomethyl)ethyl]-6-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate.

Provenance & Evidence