Trifluoroacetic acid → HCID 86575001, compound

Participants

Reaction Steps

To a solution of 1-tert-butyl 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((E)-3-((4-fluorophenyl)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 (250 mg, 0.323 mmol), TFA (1 mL, 12.98 mmol) in dichloromethane (4 mL) stirred at rt. The reaction mixture was stirred at rt for 2 h, washed with saturated NaHCO3 in water (300 mL×8); followed by 2 M HCl (300 mL), water, and then brine. The organic layer was dried over Na2SO4, filtered and concentrated to give the crude product, which was solved into DCM (80 mL) and hexane (120 mL) was added. The suspension was filtered, washed with hexane to afford the crude product, and then purified by preparative-HPLC to afford the title compound (160 mg, 68%) as a light white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ=7.56 (br. s., 3H), 7.23-6.93 (m, 3H), 5.96-5.75 (m, 1H), 4.52 (dd, J=5.1, 10.9 Hz, 1H), 3.33-3.13 (m, 1H), 2.88-2.51 (m, 3H), 2.45-0.72 (m, 47H); LC/MS: m/z calculated 717.4. Found 718.3 (M+1)+.

Provenance & Evidence