Sodium Hydroxide → 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-(thiophen-3-ylmethylamino)-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)benzoic acid

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-(thiophen-3-ylmethylamino)-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 (32 mg, 0.050 mmol) in dioxane (1 mL) was added NaOH (1N) (0.250 mL, 0.250 mmol). The mixture was heated to 85° C. for 15 h. The mixture was cooled to rt and was purified by prep HPLC to give the title compound (18 mg, 0.027 mmol, 53.5% yield) as a white solid. LCMS: m/e 626.5 (M+H)+, 1.82 min (method 2). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.00 (2H, d, J=8.3 Hz), 7.30 (1H, dd, J=4.8, 3.0 Hz), 7.24 (2H, d, J=8.3 Hz), 7.20 (1H, d, J=2.0 Hz), 7.12 (1H, dd, J=5.0, 1.0 Hz), 5.30-5.34 (1H, m), 4.72 (1H, d, J=1.8 Hz), 4.61 (1H, s), 2.61 (1H, td, J=10.7, 5.4 Hz), 1.89-2.17 (5H, m), 1.77-1.88 (1H, m), 1.72 (3H, s), 1.14 (3H, s), 1.02 (3H, s), 1.00 (3H, s), 0.94-1.74 (18H, m), 0.96 (6H, s).

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