Ethyl 1-aminocyclopropane-1-carboxylate hydrochloride → 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(3-(1-carboxycyclopropyl)ureido)-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)benzoic acid

참여 물질

반응 단계

The title compound was prepared in 25% yield from methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-isocyanato-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 same procedure as described for the preparation of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(3-(2-(dimethylamino)ethyl)ureido)-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)benzoic acid, except 1-aminocyclopropane-1-carboxylic acid ethyl ester hydrochloride was used instead of N,N-dimethylethylenediamine in Step 1. LCMS: m/e 657.3 (M+H)+, 4.18 min (method 8). 1H NMR (500 MHz, MeOD) δ ppm 7.9 (2H, d, J=8.2 Hz), 7.2 (2H, d, J=8.2 Hz), 5.3-5.3 (1H, m), 4.8 (1H, br. s.), 4.6 (1H, br. s.), 3.7-3.8 (1H, m), 3.6-3.6 (1H, m), 3.5-3.6 (1H, m), 2.5-2.7 (2H, m), 2.4 (1H, dd, J=12.1, 8.4 Hz), 2.2 (1H, dd, J=17.1, 6.4 Hz), 2.0 (1H, d, J=11.9 Hz), 1.9 (2H, dt, J=6.6, 3.2 Hz), 1.8-1.9 (2H, m), 1.7-1.8 (4H, m), 1.4-1.7 (7H, m), 1.4 (3H, td, J=13.1, 4.0 Hz), 1.3 (3H, t, J=11.7 Hz), 1.2 (3H, s), 1.1-1.1 (3H, m), 1.1 (3H, d, J=2.4 Hz), 1.0 (3H, s), 1.0 (2H, s), 0.9 (1H, m).

출처 및 근거