2-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-[[3-(1,1-dioxo-1,4-thiazinan-4-yl)propylamino]methyl]-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]spiro[3.3]hept-2-ene-6,6-dicarboxylic acid → ethyl 4-((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)-2-methylcyclohexa-1,3-dienecarboxylate

Participants

Reaction Steps

The title compound was prepared following the method described above in Step 2 for the preparation of 6-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(((3-(1,1-dioxidothiomorpholino)propyl)amino)methyl)-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)spiro[3.3]hept-5-ene-2,2-dicarboxylic acid (example A14), using ethyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-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)-2-methylcyclohexa-1,3-dienecarboxylate as the reactant. (quantitative yield). MS: m/e 735.8 (M+H)+, 3.41 min (method 3). 1H NMR (400 MHz, CHLOROFORM-d) δ 5.65 (s, 1H), 5.28 (dd, J=6.0, 1.5 Hz, 1H), 4.71 (s, 1H), 4.59 (s, 1H), 4.19 (q, J=7.1 Hz, 2H), 3.15-2.97 (m, 8H), 2.73-2.51 (m, 4H), 2.50-2.38 (m, 3H), 2.22 (q, J=8.3 Hz, 2H), 2.15 (s, 3H), 2.06-1.18 (m, 25H), 1.11-1.04 (m, 6H), 1.00 (s, 3H), 0.98-0.95 (m, 6H), 0.88 (s, 3H).

Provenance & Evidence