Lithium Hydroxide → {4-[6-(4-tert-Butylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenoxy}-acetic acid

Participants

Reaction Steps

To a solution of {4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenoxy}-acetic acid methyl ester (0.1727 g, 0.356 mmol) in tetrahydrofuran (5 mL) was added LiOH (1 mL of a 4M solution) and the mixture was stirred at ambient temperature for 18 h. The solvent was removed under reduced pressure and the residue was taken up in water, brought to pH 4 and the solid filtered to the title compound. 1H-NMR (DMSO-d6, 400 MHz): δ 12.97 (s, broad, 1H), 12.72 (d, J=24.76 Hz, 1H), 10.11 (d, J=15.16 Hz, 1H), 10.11 (d, J=15.16 Hz, 1H), 8.31 (s, 0.5H), 8.06 (s, 0.5H), 7.75-7.81 (m, 1H), 7.63-7.71 (m, 2.5H), 7.51 (d, J=8.34 Hz, 0.5H,) 7.30 (d, J=8.59 Hz, 2H), 6.71 (s, 2H), 4.68 (s, 2H), 2.03 (s, 6H), 1.22 (s, 9H). MS (m/z) 472.2 (M+1).

Provenance & Evidence