Reacción #172800

Ecuación de reacción

methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxido-4-thiomorpholinyl)ethyl)amino)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-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

sodium hydroxide

→

title compound

Rendimiento 40.8%

4-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-[[2-(1,1-dioxido-4-thiomorpholinyl)ethyl]amino]-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-5a,5b,8,8,11a-pentamethyl-1-(1-methylethenyl)-1H-cyclopenta[a]chrysen-9-yl]-benzoic acid

Rendimiento 40.8%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe reaction was filtered
2. 2
   Otrothe resulting clear solution was purified by prep HPLC

Procedimiento

A mixture of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxido-4-thiomorpholinyl)ethyl)amino)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-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 (500 mg, 0.709 mmol) and aqueous sodium hydroxide 10N (1.42 mL, 14.2 mmol) in dioxane (10 mL) was heated at 78° C. for 3 h. The reaction was filtered and the resulting clear solution was purified by prep HPLC to provide the title compound as white solid (200 mg, 39%). LCMS: m/e 691.59 (M+H)+, 2.53 min (method 10). 1H NMR (500 MHz, Acetic acid d4) δ ppm 8.04 (d, J=8.24 Hz, 2H), 7.30 (d, J=8.24 Hz, 2H), 5.45-5.34 (m, 1H), 4.85 (s, 1H), 4.74 (s, 1H), 3.55-3.40 (m, 1H), 3.39-3.22 (m, 6H), 3.22-3.11 (m, 4H), 3.11-3.03 (m, 1H), 3.04-2.94 (m, 1H), 2.36-1.18 (m, 22H), 1.76 (s, 3H), 1.30 (s, 3H), 1.15 (s, 3H), 1.12 (s, 3H), 1.03 (s, 3H), 1.00 (s, 3H).

Fuente