1,3-Cyclohexadiene → 6-((4-(cyclopropyl((3aS,9R,9aR)-7-fluoro-4-(4-(trifluoromethoxy)benzoyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]quinolin-9-yl)amino)-4-oxobutanoyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Palladium on carbon (80 mg, 0.752 mmol) was added to a stirred mixture of benzyl 6-((4-(cyclopropyl((3aS,9R,9aR)-7-fluoro-4-(4-(trifluoromethoxy)benzoyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]quinolin-9-yl)amino)-4-oxobutanoyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate (0.23 g, 0.29 mmol) and cyclohexadiene (1.5 mL, 0.293 mmol) in isopropanol (7.5 mL) and cyclopentylmethyl ether (7.50 mL) and the mixture was stirred at 60° C. for 1 h. The mixture was filtered through a Celite® pad and washed with ether/isopropanol (1/1). Solvent was removed to give crude product which was purified using reverse phase HPLC to give 6-((4-(cyclopropyl((3aS,9R,9aR)-7-fluoro-4-(4-(trifluoromethoxy)benzoyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]quinolin-9-yl)amino)-4-oxobutanoyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid 174 (140 mg), [M+H]+=710.1.

Provenance & Evidence