Hydroquinone → HCID 56975877, compound

Participants

Reaction Steps

To a solution of 4-nitrobenzyl 2-[(3S,4R)-4-{2-(1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-2-oxoethyl}-3-{(1R)-1-trimethylsilyloxyethyl}-2-oxoazetidin-1-yl]-2-oxoacetate (4.73 g) and triethyl phosphite (6.2 ml) in toluene (70 ml) was heated under reflux for 2 hours under nitrogen atmosphere. To this solution was added hydroquinone (800 mg), and the reflux was continued for additional 6 hours. The solvent was removed in vacuo to give a residue, which was chromatographed on silica gel (400 ml) eluting with a mixture of hexane and ethyl acetate (4:1 v/v) to give 4-nitrobenzyl (5R,6S)-3-(1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-6-[(1R)-1-trimethylsilyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (3.77 g).

Provenance & Evidence