HCID 86731493, compound → (1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-9-(2-carboxyethyl)-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]chrysene-3a-carboxylic acid

Participants

Reaction Steps

A mixture of (E)-3-((1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-3a-(benzyloxycarbonyl)-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)acrylic acid (20 mg, 0.033 mmol) and 10% Pd/C (25 mg, 0.023 mmol) in MeOH (0.5 mL) and ethyl acetate (1 mL) was connected to a balloon of hydrogen and stirred at room temperature for 5 hours. The reaction mixture was filtered to remove Pd/C and the filtrates were concentrated under reduced pressure. The residue was dissolved in DMF and purified by prep HPLC to provide the desired product (1.59 mg, 9%). LCMS: m/e 509.6 (M−H)−, 2.36 min (method 6). 1H NMR (400 MHz, <DMSOmix>) δ 5.21 (d, J=5.0 Hz, 1H), 4.70 (br. s., 1H), 4.57 (br. s., 1H), 3.05-0.98 (m, 27H), 1.67 (s., 3H), 0.96 (s., 6H), 0.93 (s., 3H), 0.89 (s., 3H), 0.79 (s., 3H).

Provenance & Evidence