Sodium Hydroxide → HCID 57586446, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-{3-[6-(3,5-dibromo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (1.5 g, 2.33 mmol) in ethanol (30 mL) was added aqueous 1 N sodium hydroxide (25 mL) at room temperature. The resulting suspension was heated to 50-55° C. and the mixture was stirred for 3 h. Then, the reaction mixture was concentrated and the residue was diluted with water (20 mL) and extracted with diethyl ether (50 mL) to remove any neutral impurities. The aqueous layer was acidified with 1 N hydrochloric acid and the organic compound was extracted into ethyl acetate (2×50 mL). The combined ethyl acetate extracts were washed with brine solution (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated to give the crude product which was purified by using an ISCO 40 g column, eluting with 0-100% ethyl acetate/hexanes to isolate 4-{2-(2-carboxy-ethyl)-3-[6-(3,5-dibromo-phenoxy)-hexyl]-phenoxy}-butyric acid (1.26 g, 92%) as a white solid: ES(+)-HRMS m/e calculated for C25H30Br2O6 (M+Na)+ 607.0301, found 607.0298.

Provenance & Evidence