Lithium hydroxide, monohydrate → 3-[4-({[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[2-(1H-indol-3-yl)ethyl]-amino}-methyl)-phenyl]-acrylic acid

Participants

Reaction Steps

To a stirred solution of compound 3 (3.18 g, 6.45 mmol) in THF (40 mL) was added a solution of LiOH.H2O (677 mg, 16.14 mmol) in water (20 mL) at room temperature. After 24 h the reaction mixture was concentrated, diluted with water and acidified with 1N HCl until a pH 5-6. A precipitate was formed which was separated by filtration, rinsed with water and dried to afford the title compound 4 (2.43 g, 5.08 mmol, 79% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ(ppm): 12.34 (bs, 1H), 10.75 (s, 1H), 7.63 (d, J=8.2 Hz, 2H), 7.59 (d, J=15.8 Hz, 1H), 7.44-7.35 (m, 3H), 7.32 (d, J=8.0 Hz, 1H), 7.11 (d, J=2.3 Hz, 1H), 7.05 (td, J=7.5, 1.0 Hz, 1H), 6.92 (td, J=7.4, 0.9 Hz, 1H), 6.51 (d, J=15.8 Hz, 1H), 3.79 (s, 2H), 3.69 (t, J=6.4 Hz, 2H), 2.93-2.74 (m, 4H), 2.69 (t, J=6.2 Hz, 2H), 0.88 (s, 9H), 0.05 (s, 6H).

Provenance & Evidence