4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)-2-oxoethylamino)-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 → 1-(2-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-carboxyphenyl)-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-3a-yl)amino)ethyl)piperidine-4-carboxylic acid

Participants

Reaction Steps

The title compound was prepared following the method described above for the synthesis of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)-2-oxoethylamino)-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 using methyl 1-(2-chloroethyl)piperidine-4-carboxylate hydrochloride (prepared as described below) as the alkylating reagent in Step 1. The product was isolated as a white solid (8 mg, 83%). LCMS: m/e 685.6 (M+H)+, 2.33 min (method 10). 1H NMR (400 MHz, METHANOL-d4) δ 7.94 (d, J=8.3 Hz, 2H), 7.23 (d, J=8.3 Hz, 2H), 5.31 (d, J=4.5 Hz, 1H), 4.86 (s, 1H), 4.74 (s, 1H), 3.48-3.36 (m, 5H), 3.12-2.88 (m, 2H), 2.79-2.69 (m 1H), 2.68-2.60 (m, 1H), 2.24-2.11 (m, 4H), 2.11-2.00 (m, 4H), 1.97-1.81 (m, 3H), 1.77 (s, 3H), 1.81-1.71 (m, 2H), 1.70-1.46 (m, 10H), 1.45-1.27 (m, 4H), 1.21 (s, 3H), 1.12 (s, 3H), 1.06 (s, 3H), 0.98 (s, 3H), 0.97 (s, 3H).

Provenance & Evidence