Trifluoroacetic acid → HCID 71611455, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-tert-butyl 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((E)-3-(((R)-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 (400 mg, 0.489 mmol) in DCM (10 mL) that was stirred at room temp was then added TFA (5 mL, 64.9 mmol). The reaction mixture was stirred at 30° C. for 2 h. The mixture was evaporated to dryness then diluted with 200 mL DCM. The organic phase was washed with saturated NaHCO3, water and brine. The organics were dried and concentrated under reduced pressure to afford crude product which was purified by preparative-HPLC to afford the title compound (100 mg, 27%) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ=7.38-7.14 (m, 4H), 6.96 (d, J=15.8 Hz, 1H), 6.25 (d, J=7.8 Hz, 1H), 5.73 (d, J=15.6 Hz, 1H), 5.23-5.08 (m, 1H), 4.50 (dd, J=5.4, 10.7 Hz, 1H), 3.27-3.11 (m, 1H), 2.82-2.49 (m, 3H), 2.33-2.19 (m, 1H), 2.19-2.00 (m, 2H), 2.00-0.71 (m, 47H); LC/MS: m/z calculated 761.4. Found 762.2 (M+1)+.

Provenance & Evidence