Sodium Hydroxide → RO5101576

Participants

Reaction Conditions

Reaction Steps

To a solution of the 4-{3-[6-(3-benzo[1,3]dioxol-5-yl-5-thiophen-3-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (649 mg, 0.944 mmol) in ethanol (40 mL) was added aqueous 1.0 N sodium hydroxide (35 mL) at room temperature. The resulting suspension was heated to 50-55° C. and the mixture was stirred for 5 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 1.0 N hydrochloric acid and the precipitated white organic compound was extracted into ethyl acetate (2×100 mL). The combined ethyl acetate extracts were washed with brine solution (100 mL) and the organic layers were dried over anhydrous magnesium sulfate. Filtration and removal of the solvent afforded the crude product which was dissolved in hot iso-propyl acetate (10 mL) and then diluted with hexanes (5 mL). The resulting light yellow solution was stored in the refrigerator for 2 days. The white solids were collected by filtration and washed with hexanes. After air-drying, 4-{3-[6-(3-benzo[1,3]dioxol-5-yl-5-thiophen-3-yl-phenoxy)-hexyl]-2-(2-carboxy-ethyl)-phenoxy}-butyric acid (404 mg, 68%) was isolated as a white solids, mp=110-112° C.: ES(+)-HRMS m/e calculated for C36H38O8S (M+Na)+ 653.2179, found 653.2183. Elemental analysis: (C36H38O8S): C=68.49 (calcd, 68.55), H=5.93 (6.07), S=5.15 (5.08).

Provenance & Evidence