Trifluoroacetic acid → 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((3-morpholinopropylamino)methyl)-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid

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Reaction Steps

To a solution of tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((3-morpholinopropylamino)methyl)-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate (69 mg, 0.095 mmol) in DCM (1 ml) was added TFA (0.4 ml, 5.19 mmol). The mixture was stirred at rt for 3 h then was concentrated under reduced pressure. The residue was purified by prep. HPLC. The fractions containing the expected product were combined and concentrated under reduced pressure to afford the title compound (36 mg, 0.054 mmol, 56.5% yield) as a white foam. LCMS: m/e 671.5 (M+H)+, 2.17 min (method 6). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.94 (d, J=8.03 Hz, 2H),7.15 (d, J=8.03 Hz, 2H), 5.29 (d, J=4.52 Hz, 1H), 4.71 (br. s., 1H), 4.62 (br. s., 1H), 3.73 (br. s., 4H), 3.09-3.26 (m, 3H), 2.65 (d, J=12.30 Hz, 1H), 2.56 (br. s., 6H), 2.42 (br. s., 1H), 1.69 (s, 3H), 1.07 (s, 3H), 1.05-2.14 (m, 24H), 1.00 (s, 3H), 0.97 (s, 3H), 0.93 (br. s., 3H), 0.93 (br. s., 3H).

Provenance & Evidence