Trifluoroacetic acid → HCID 71611167, compound

Participants

Reaction Steps

To a solution of 1-tert-butyl 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((E)-3-(((S)-1-(3-chlorophenyl)ethyl)amino)-3-oxoprop-1-en-1-yl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl) 2,2-dimethylsuccinate (12 g, 14.66 mmol) in dichloromethane (130 mL) was added TFA (80 mL, 14.66 mmol). The reaction mixture was stirred at rt for 2 hr and diluted with DCM, washed with water twice. And the organic layer was concentrated, diluted with MeCN/H2O (1:5, 36 mL) and freeze-dried under high vacuo to give the title compound (9.9 g, 12.89 mmol, 88%). This material was combined with several batches made under similar conditions and freeze dried together for characterization (31 g, 41 mmol) as a light yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ=7.38-7.13 (m, 4H), 6.97 (d, J=15.6 Hz, 1H), 5.82-5.59 (m, 2H), 5.26-5.06 (m, 1H), 4.50 (dd, J=5.3, 11.0 Hz, 1H), 3.29-3.09 (m, 1H), 2.81-2.48 (m, 3H), 2.37-2.00 (m, 3H), 2.00-0.68 (m, 47H).

Provenance & Evidence