Acetonitrile → Trifluoroacetic acid

Participants

Reaction Steps

To a solution of 1-tert-butyl 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3a-((E)-3-oxo-3-(pyridin-2-ylamino)prop-1-en-1-yl)-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 (300 mg, 0.396 mmol) in dichloromethane (6 mL) was added TFA (3 mL, 0.396 mmol). The reaction mixture was stirred at rt for 2 hr and evaporated in vacuo to afford crude product which was purified by preparative-HPLC (Mobile Phase: A=0.05% TFA/H2O, B=MeCN) to give the title compound trifluoroacetic acid salt (100 mg, 0.119 mmol, 30.0%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=10.72 (br. s., 1H), 8.33 (br. s., 1H), 8.14 (br. s., 1H), 7.83 (br. s., 1H), 7.33-6.97 (m, 1H), 6.97-6.75 (m, 1H), 6.41-6.13 (m, 1H), 4.52-4.25 (m, 1H), 3.35-3.06 (m, 1H), 2.98-2.65 (m, 2H), 2.35-0.53 (m, 47H); LC/MS: m/z calculated 700.5. Found 701.3 (M+1)+.

Provenance & Evidence