Sodium Hydroxide → (S)-4-((1R,3 aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-((1S,4S)-2,2-dioxido-2-thia-5-azabicyclo[2.2.1]heptan-5-yl)ethyl)amino)-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)cyclohex-3-enecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-benzyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-((1S,4S)-2,2-dioxido-2-thia-5-azabicyclo[2.2.1]heptan-5-yl)ethyl)amino)-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)cyclohex-3-enecarboxylate (5 mg, 6.27 μmol) and sodium hydroxide (0.063 mL, 0.063 mmol) in acetonitrile (1 mL) was heated up at 80° C. for 3 hours. The reaction mixture was filtered and purified by HPLC to provide (S)-4-((1R,3 aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-((1S,4S)-2,2-dioxido-2-thia-5-azabicyclo[2.2.1]heptan-5-yl)ethyl)amino)-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)cyclohex-3-enecarboxylic acid (2.2 mg, 47% yield) as a white solid. LCMS: m/e 707.8 (M+H)+, 1.82 min (method 5). 1H NMR (400 MHz, Acetic) δ 5.37 (br. s., 1H), 5.22 (d, J=4.3 Hz, 1H), 4.80 (s, 1H), 4.70 (s, 1H), 4.10 (br. s., 1H), 3.79-3.65 (m, 1H), 3.50-3.32 (m, 3H), 3.28-3.00 (m, 5H), 2.93-2.75 (m, 1H), 2.56 (d, J=12.3 Hz, 2H), 2.49-2.39 (m, 1H), 2.32 (br. s., 2H), 2.23-1.10 (m, 26H), 1.72 (s, 3H), 1.16 (s, 3H), 1.07 (s, 3H), 1.00 (s, 3H), 0.94 (s, 3H), 0.92 (s, 3H).

Provenance & Evidence