Hydrochloric Acid → [Rac]-3-{4-[2-(4-tert-butyl-phenyl)-thiazol-4-ylmethoxy]-3-methyl-phenyl}-2-ethoxy-propionic acid

Participants

Reaction Conditions

Reaction Steps

140 mg of [rac]-3-{4-[2-(4-tert-butyl-phenyl)-thiazol-4-ylmethoxy]-3-methyl-phenyl}-2-ethoxy-propionic acid ethyl ester (0.29 mmol) were dissolved in 5 ml of methanol; 1 ml of a 2N aqueous lithium hydroxide solution was added and the reaction mixture was stirred at 55° C. for 1 h. After cooling to room temperature, 1 ml of a 2N aqueous hydrochloric acid solution and 0.5 ml of a saturated solution of potassium hydrogen sulfate were added. The reaction mixture was then extracted with two 10 ml portions of dichloromethane. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate and evaporated, leaving 130 mg (98.6% of theory) of [rac]-3-{4-[2-(4-tert-butyl-phenyl)-thiazol-4-ylmethoxy]-3-methyl-phenyl}-2-ethoxy-propionic acid as a colorless solid.

Provenance & Evidence