Reaction Steps
A mixture of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-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 (600 mg, 1.10 mmol), 4-(2-chloroethyl)thiomorpholine 1,1-dioxide (600 mg, 2.56 mmol) (prepared as described in WO2002045652), anhydrous potassium phosphate (3.00 g, 14.1 mmol) and potassium iodide (10 mg, 0.060 mmol) in acetonitrile (50 mL) was placed in 150 mL AceGlass resealable pressure vessel. The white suspension was blanketed with nitrogen. The vessel was sealed and warmed to 115-125° C. for 48 h. The crude reaction was filtered through a short bed of silica gel and washed with ethyl acetate. The filtrate was concentrated in vacuo and purified by silica gel chromatography eluted with ethyl acetate and hexanes (0-50%) to afford the title compound as a colorless foam (566 mg, 73%). 1H NMR (500 MHz, CHLOROFORM-d) δ 7.95 (d, J=8.2 Hz, 2H), 7.22 (d, J=8.2 Hz, 2H), 5.31 (d, J=4.6 Hz, 1H), 4.74 (d, J=1.8 Hz, 1H), 4.62 (s, 1H), 3.93 (s, 3H), 3.22-2.99 (m, 9H), 2.79-2.55 (m, 4H), 2.52-2.42 (m, 1H), 2.18-2.09 (m, 1H), 1.99-1.02 (m, 20H), 1.72 (s, 3H), 1.11 (s, 3H), 1.01 (s., 3H), 1.10 (s, 3H), 0.95 (s, 3H), 0.95 (s., 3H). LCMS: m/e 705.51 (M+H)+, 3.01 min (method 10).
