Triethylsilane → 2-((4-Oxo-8-(3-(2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

Participants

Reaction Steps

To tert-butyl 2-((4-oxo-8-(3-(2′-oxospiro[cyclopropane-1,3′-indoline]-1′-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.18 g, 0.29 mmol) was added concentrated formic acid (3 mL) and triethylsilane (0.05 mL). After stirring at room temperature for 18 hours, the reaction mixture was concentrated, taken in 4M HCl in dioxane and lyophilized to obtain the title compound as a hydrochloride salt (0.165 g, 95%); 1H NMR (DMSO-d6): δ 1.52-1.63 (m, 4H), 1.98 (d, 2H, J=14.8 Hz), 2.08-2.10 (m, 2H), 2.92 (t, 2H, J=7.6 Hz), 3.21 (br, 2H), 3.45-3.71 (m, 4H), 3.84 (t, 2H, J=6.8 Hz), 4.68 (s, 2H), 4.92 (s, 2H), 6.80 (t, 1H, J=7.6 Hz), 6.98-7.05 (m, 4H), 7.20-7.32 (m, 5H), 7.42 (t, 1H, J=7.6 Hz), 7.57 (t, 1H, J=7.6 Hz), 7.92 (dd, 1H, J=8 and 1.6 Hz), 10.32 (br, 1H), 13.19 (s, 1H); MS for C34H36N4O4 m/z 565.14 (M+H)+.

Provenance & Evidence