Sodium Hydroxide → 4-((((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-(tert-butoxycarbonyl)phenyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-3a-yl)methyl)(2-(dimethylamino)ethyl)amino)-4-oxobutanoic acid

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Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((N-(2-(dimethylamino)ethyl)-4-methoxy-4-oxobutanamido)methyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate (53 mg, 0.068 mmol) in 1,4-dioxane (1 ml) was added NaOH (0.338 ml, 0.338 mmol). The mixture was heated to 75° C. for 3 h. The mixture was cooled to rt and was quenched with 1N HCl (3 ml) and extracted with dichloromethane (3×7 ml). The combined organic layers were dried with Na2SO4, were filtered, and concentrated under reduced pressure. The crude product was used in the next step with no additional purification. LCMS: m/e 771.6 (M+H)+, 2.70 min (method 6).

Provenance & Evidence