Trifluoroacetic acid → HCID 71611454, compound

Participants

Reaction Steps

To a solution of 1-tert-butyl 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((E)-3-((1-(3-chlorophenyl)cyclopropyl)amino)-2-methyl-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 (280 mg, 0.332 mmol) in DCM (6 mL) was added TFA (3 mL, 0.332 mmol). The reaction mixture was stirred at rt for 2 hr and evaporated in vacuo to afford crude product. This was diluted with DCM (30 mL), and washed with water, saturated NaHCO3, water, saturated NH4CI and then water. The organic layer was dried over Na2SO4, filtered and concentrated to obtain a residue, which was dissolved into MeCN— H2O (1:2, 9 mL) and freeze-dried to give the title compound (130 mg, 48%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=12.16 (br. s., 1H), 8.62 (s, 1H), 7.34-7.17 (m, 2H), 7.14 (s, 1H), 7.05 (d, J=7.5 Hz, 1H), 6.57 (s, 1H), 4.40 (dd, J=4.4, 10.9 Hz, 1H), 3.23-3.08 (m, 1H), 2.83-0.62 (m, 57H); LC/MS: m/z calculated 787.5. Found 788.2 (M+1)+.

Provenance & Evidence