Reaction Steps
5-((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)penta-2,4-dienoic acid was prepared was prepared following the procedure described in step 2 of the preparation of 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 using the corresponding crude product from step 1 as the reactant. The title compound was obtained as a mixture of 2E,4E- and 2E,4Z-2,4-dienoic acid isomers (solid, 39%). MS: m/e 695.5 (M+H)+, 2.38 min (method 5). For 2E,4E isomer, 1H NMR (400 MHz, CHLOROFORM-d) δ 7.35-7.24 (m, 1H), 6.50 (d, J=15.3 Hz, 1H), 6.16 (dd, J=15.2, 11.2 Hz, 1H), 5.89 (d, J=15.1 Hz, 1H), 5.60 (s, 1H), 4.82 (s, 1H), 4.66 (s, 1H), 3.38-2.52 (m, 12H), 2.87 (s, 3H), 2.33-0.83 (m, 24H), 1.71 (s, 3H), 1.13 (s, 3H), 0.99 (s, 3H), 0.97 (s, 3H), 0.89 (s, 3H), 0.68 (s, 3H).
