(R)-tert-butyl 2-(4-oxo-8-(3-(2-oxoindolin-1-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)-2-phenylacetate → (R)-2-(4-oxo-8-(3-(2-oxoindolin-1-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)-2-phenylacetic acid

Participants

Reaction Steps

A solution of (R)-tert-butyl 2-(4-oxo-8-(3-(2-oxoindolin-1-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)-2-phenylacetate (257 mg, 0.453 mmol, 1 equiv) in 4M hydrogen chloride solution in dioxane was stirred at ambient temperature for 5 h. The mixture was concentrated in vacuo and purified using preparative thin layer chromatography in 10% methanol in dichloromethane. The purified mixture was treated with 4M hydrogen chloride solution in dioxane to afford the hydrogen chloride salt of the title compound as a cream powder (100 mg, 28%); 1H NMR (400 MHz, DMSO-d6): δ 1.94 (m, 2H); 2.07 (m, 2H); 2.85 (m, 2H); 3.14 (m, 2H); 3.49-3.52 (m, 4H); 3.76 (t, 2H, J=6.8 Hz); 4.17 (d, 1H, J=5.2 Hz); 4.87 (d, 1H, J=4.8 Hz); 5.79 (s, 1H); 6.85 (m, 1H); 6.97-7.04 (m, 3H); 7.12 (d, 1H, J=7.6 Hz); 7.21 (t, 1H, J=7.6 and 8.4 Hz); 7.28 (dd, 2H, J=5.6 and 6 Hz); 7.42-7.45 (m, 6H) 10.6 (bs, 1H); 13.4 (bs, 1H); MS for C32H34N4O4 m/z 539 (M+H)+.

Provenance & Evidence