HCID 68008794, compound → HCID 68009052, compound

Participants

Reaction Steps

A solution of (2R,6S,13aS,14aR,16aS,E)-ethyl 6-(tert-butoxycarbonylamino)-12,12-difluoro-2-hydroxy-5,16-dioxo-1,2,3,5,6,7,10,11,12,13,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo [1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (Example 7h, 1.06 g, 2.002 mmol) in ethyl acetate (50 ml) at 25° C. was added 10% palladium/carbon (0.170 g, 0.160 mmol). The reaction mixture was stirred under a balloon of hydrogen for 2 days. The reaction mixture was filtered through a small plug of silica gel and eluted with ethyl acetate then methanol. The solvent was evaporated under reduced pressure and the resulting solid was purified by flash chromatography on silica gel (40% ethyl acetate/dichloromethane, then ethyl acetate) to provide (2R,6S,13aS,14aR,16aS)-ethyl 6-(tert-butoxycarbonylamino)-12,12-difluoro-2-hydroxy-5,16-dioxooctadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (1.01 g, 1.900 mmol, 95% yield) as a white solid. MS (ESI): m/z=532.3 [M+H].

Provenance & Evidence