Hydrochloric Acid → 2-Methyl-3-{5-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-thiophen-2-yl}-2-phenoxy-propionic Acid

Participants

Reaction Conditions

Reaction Steps

2-Methyl-3-{5-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-thiophen-2-yl}-2-phenoxy-propionic acid methyl ester 400 mg) was dissolved in EtOH (10 mL), and then 5 N NaOH (3 mL) was added. This mixture was allowed to stir at 60° C. for 1 h. The mixture was cooled to room temperature and then acidified to pH=2 by the dropwise addition of 5 N HCl. This acidic mixture was diluted with H2O (10 mL) and then extracted with CH2Cl2 (2×25 mL). The organic layers were combined, dried over NaCl, and solvent removed in vacuo which provided 354 mg (92%) of desired acid: 1H NMR (400 MHz, CDCl3) δ 8.05 (d, 2 H), 7.39 (m, 4 H), 7.23 (m, 1 H), 7.03 (t, 1 H), 6.95 (d, 2 H), 6.70 (d, 1 H), 6.62 (d, 1 H), 3.40 (d, 1 H), 3.30 (d, 1 H), 2.80 (t, 2 H), 2.52 (t, 2 H), 2.27 (s, 3 H), 2.02 (m, 2 H), 1.44 (s, 3 H); MS (EI) 462.2 (M+H)+.

Provenance & Evidence