Acetic Acid → HCID 57160014, compound

Participants

Reaction Steps

To a solution of 1.74 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 and 0.54 ml of acetic acid in 9 ml of tetrahydrofuran was added dropwise 3.29 g of 70 % tetrabutylammonium fluoride at room temperature. The mixture was stirred for 20 hours at room temperature. 60 ml of Ethyl acetate and 45 ml of water were added to the reaction mixture and the aqueous layer was extracted three times with ethyl acetate. The extracts were combined, washed in turn with saturated aqueous sodium hydrogen carbonate and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was chromatographed on silica gel to give 766 mg of allyl (5R,6S)-3-[2-allyloxycarbonylamino-1-(N-allyloxycarbonylaminomethyl)ethyl]-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate.

Provenance & Evidence