Hydrochloric Acid → [4-(2-Chlorophenyl)-2-(4-{[(1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetic acid

Participants

Reaction Steps

Methyl [4-(2-chlorophenyl)-2-(4-{[( 1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetate (0.145 g, 0.328 mmol) was dissolved in EtOH (2 mL). NaOH (0.65 mL, 1N, 0.65 mmol) was added and the solution heated to reflux for 5 h. HCl (0.35 mL, 2N, 0.70 mmol) was added and the solvent removed. The mixture was partitioned between EtOAc and H2O. The EtOAc layer was dried (MgSO4) and the solvent removed to yield [4-(2-chlorophenyl)-2-(4-{[(1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetic acid (0.138 g) as a white solid. mp 101-103° C. 1H NMR (500 MHz, DMSO-d6) δ: 0.88 (t, 6H, J=7.3 Hz), 1.50 (m, 2H), 1.55 (m, 2H), 3.42 (s, 2H), 3.82 (m, 1H), 7.35 (m, 1H), 7.42 (m, 3H), 7.58 (m, 3H), 7.96 (d, 2H, J=8.4 Hz), 8.11 (d, 1H, J=8.7 Hz). MS (ES) m/z 442.1 ([M+H]+). MS (ES) m/z 883.1 ([2M+H]+). Anal. Calcd for C24H24ClNO3S: C, 65.22; H, 5.47; N, 3.17. Found: C, 62.33; H, 5.54; N, 3.01.

Provenance & Evidence