Reaction Steps
1-fluoro-4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(4-(methylsulfonyl)piperidin-1-yl)ethyl)amino)-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)methylene)cyclohexanecarboxylic acid was prepared following the method described above for the preparation of 1-((tert-butoxycarbonyl)amino)-2-((E)-2-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)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)vinyl)cyclopropanecarboxylic acid, using ethyl 1-fluoro-4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(4-(methylsulfonyl)piperidin-1-yl)ethyl)amino)-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)methylene)cyclohexanecarboxylate as the reactant in step 2. The reaction crude was purified by prep HPLC (method 4) to afford the title compound as a mixture of isomers in 20.7% of yield. MS: m/e 755.5 (M+H)+, 2.610 min (method 4). 1H NMR (400 MHz, METHANOL-d4) δ 5.95-5.35 (m, 1H), 5.32-5.12 (m, 1H), 4.79 (br. s., 1H), 4.71 (s, 1H), 3.25-3.04 (m, 5H), 2.96 (s, 3H), 2.90-1.81 (m, 24H), 1.76 (s, 3H), 1.73-1.27 (m, 15H), 1.22 (br. s., 3H), 1.13-1.08 (m, 3H), 1.07-0.91 (m, 6H), 0.90-0.83 (m, 3H); 19F NMR (376 MHz, METHANOL-d4) δ −154.27-167.89 (m, 1F).
