Sodium Hydroxide → 4-{2-(2-Carboxy-ethyl)-3-[6-(3-methanesulfonyl-5-thiazol-2-yl-phenoxy)-hexyl]-phenoxy}-butyric Acid

Participants

Reaction Conditions

Reaction Steps

To a solution containing 4-{2-(2-ethoxycarbonyl-ethyl)-3-[6-(3-iodo-5-methanesulfonyl-phenoxy)-hexyl]-phenoxy}-butyric acid ethyl ester (90 mg, 0.14 mmol) and 2-(tributylstannyl)thiazole (0.088 mL, 0.28 mmol) in toluene (4 mL) was added Pd(PPh3)4 (8 mg, 5 mol %). The reaction mixture was stirred at 110° C. for 12 h, then diluted with EtOAc. The resulting solution was washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford a crude sample which was dissolved in hot ethanol (4 mL). To this solution, 1 N sodium hydroxide (1 mL) was added and the reaction mixture was stirred at 60° C. for 3 h. Once the hydrolysis was completed as determined by LCMS, the reaction mixture was diluted with EtOAc and washed with 10% HCl and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford a crude sample which was purified by preparative HPLC. HR-ES(+) m/e calcd for C29H35NO8S2 (M+H)+ 590.1877, found 590.1876.

Provenance & Evidence