Hydrochloric Acid → 2-((8-(3-(3,3-Dimethyl-2-oxoindolin-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

Participants

Reaction Steps

To tert-butyl 2-((8-(3-(3,3-dimethyl-2-oxoindolin-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.17 g, 0.27 mmol) was added 4M solution of HCl in dioxane (3 mL) and triethylsilane (0.1 mL). After stirring at room temperature for 4 hours, the reaction mixture was concentrated in vacuo, washed with acetonitrile and lyophilized in acetonitrile/water (1:1) to obtain the title compound as a hydrochloride salt (0.8 g); 1H NMR (DMSO-d6): δ 1.28 (s, 6H), 1.98 (d, 2H, J=10.4 Hz), 2.07 (t, 2H, J=6.4 Hz), 2.90-2.96 (m, 2H), 3.27 (br, 2H), 3.54-3.61 (m, 4H), 3.77 (t, 2H, J=6.8 Hz), 4.66 (s, 2H), 4.92 (s, 2H), 6.80 (t, 1H, J=7.2 Hz), 6.98 (d, 2H, J=8 Hz), 7.06 (t, 1H, J=7.6 Hz), 7.16 (d, 1H, J=7.6 Hz), 7.20-7.32 (m, 4H), 7.37 (d, 1H, J=7.2 Hz), 7.42 (t, 1H, J=8 Hz), 7.57 (t, 1H, J=7.6 Hz), 7.92 (d, 1H, J=8 Hz), 10.21 (br, 1H), 13.19 (br, 1H); MS for C34H38N4O4 m/z 567.22 (M+H)+.

Provenance & Evidence