Lithium Hydroxide → HCID 67036258, compound

Participants

Reaction Steps

A solution of 3-{3-[1-(4-chloro-phenyl)-2-methyl-propylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester (0.40 g, 0.90 mmol) was dissolved in THF 15 ml. Then a solution of lithium hydroxide (0.38 g, 9.0 mmol) in water (3.0 ml) was added. After stirring for 12 hours, the solvent was removed under reduced pressure. The residue was dissolved in 2 ml DMF for prepared HPLC to give 3-{3-[1-(4-chloro-phenyl)-2-methyl-propylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid as a yellow powder (200 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.00 (d, J=6.82 Hz, 6H) 4.90-4.99 (m, 1H) 5.05 (s, 2H) 5.59 (d, J=7.83 Hz, 1H) 6.64 (t, J=7.71 Hz, 1H) 6.91 (d, J=7.83 Hz, 1H) 7.10 (t, J=7.71 Hz, 1H) 7.27 (d, J=8.34 Hz, 2H) 7.49 (t, J=7.58 Hz, 1H) 7.63 (d, J=8.34 Hz, 2H) 7.59 (d, J=7.58 Hz, 1H) 7.85 (d, J=7.58 Hz, 1H) 7.92 (s, 1H) 13.05 (s, 1H). MS calcd. for C26H22ClNO3 431.5, obsd. (ESI+) [(M+H)+] 432.0.

Provenance & Evidence