Reaction Steps
4-((1R,3 aS,5aR,5bR,7aR,11 aS,11bR,13 aR,13bR)-5a,5b,8,8,11a-Pentamethyl-3a-((2-(6-(methylsulfonamido)-3-azabicyclo[3.1.0]hexan-3-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)benzoic acid was prepared in 12% yield over three steps from methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(aziridin-1-yl)-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)benzoate following the method used in the preparation of 4-((1R,3 aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-((1R,5S)-6-(methylsulfonyl)-3,6-diazabicyclo[3.1.1]heptan-3-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)benzoic acid; except in step 1 tert-butyl 3-azabicyclo[3.1.0]hexan-6-ylcarbamate was used instead of (1R,5S)-tert-butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate. LC/MS: m/e 732.5 (M+H)+, 3.86 min (method 8). 1H NMR (400 MHz, 1:1 CDCl3:METHANOL-d4) δ 7.90 (d, J=8.3 Hz, 2H), 7.18 (d, J=8.3 Hz, 2H), 5.28 (d, J=4.9 Hz, 1H), 5.23 (s, 1H), 5.13 (s, 1H), 4.85 (s, 1H), 4.72 (br. s., 1H), 3.85 (br. s., 2H), 3.72 (br. s., 2H), 3.48 (br. s., 4H), 3.09 (br. s., 1H), 3.03 (s, 3H), 2.81 (d, J=10.3 Hz, 1H), 2.25-1.97 (m, 8H), 1.87 (d, J=11.5 Hz, 1H), 1.79-1.60 (m, 6H), 1.53 (d, J=16.1 Hz, 6H), 1.44-1.33 (m, 4H), 1.30-1.23 (m, 2H), 1.21 (br. s., 3H), 1.11-1.04 (m, 3H), 1.02 (s, 3H), 0.94 (s, 3H), 0.93 (br. s., 3H).
