Potassium Hydroxide → HCID 68009015, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S,6S,13aS,14aR,16aS)-ethyl 2-(benzoyloxy)-6-(tert-butoxycarbonylamino)-12,12-difluoro-5,16-dioxooctadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (Example 1d, 94.75 mg, 0.149 mmol) in ethanol (0.414 ml) at 0° C. was added dropwise a solution of KOH (0.25 ml, 0.250 mmol, 1 N in ethanol). The solution was stirred at 0° C. for 50 min and LC/MS showed completion. The reaction mixture was quenched by dropwise addition of HCl (1 N in dioxane/ethyl acetate, 0.25 ml) at 0° C. Another portion of (2S,6S,13aS,14aR,16aS)-ethyl 2-(benzoyloxy)-6-(tert-butoxycarbonylamino)-12,12-difluoro-5,16-dioxooctadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (14.36 mg) was reacted under similar condition. Materials from these two reactions were combined and purified by reverse phase HPLC (acetonitrile/water (0.1% TFA)=30/70 to 100/0, 15 min) to provide the title compound (2S,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 (91.3 mg) MS (ESI): m/z=532.2 [M+H].

Provenance & Evidence