Triphenylphosphine → 4-[3-[6-(3-Benzothiazol-5-yl-5-methanesulfonyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a mixture of benzothiazole-5-ylboronic acid pinacol ester (151.5 mg, 0.58 mmol), palladium acetate(II) (6.6 mg, 0.029 mmol), and triphenylphosphine (15.4 mg, 0.058 mmol) in dioxane (5 mL) were added 4-{2-(2-ethoxycarbonyl-ethyl)-3-[6-(3-iodo-5-methanesulfonyl-phenoxy)-hexyl]-phenoxy}-butyric acid ethyl ester (200 mg, 0.29 mmol), potassium phosphate (126.9 mg, 0.58 mmol), and water (10 mg) at room temperature under nitrogen atmosphere. Then, the brown reaction mixture was heated to 100° C. and stirred for 2 h at which time the TLC of the reaction mixture indicated the absence of starting material. Then, the reaction mixture was cooled to room temperature and diluted with water (50 mL) and ethyl acetate (50 mL). The two layers were separated and the aqueous layer was extracted with ethyl acetate (50 mL) and the combined organic extracts were washed with water (100 mL) and brine solution (100 mL). The organic layer was dried over anhydrous magnesium sulfate and filtration of the drying agent and removal of the solvent under reduced pressure gave the colored residue which was purified by using an ISCO 40 g column, eluting with 2-25% ethyl acetate in hexanes to afford 4-[3-[6-(3-benzothiazol-5-yl-5-methanesulfonyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (110 mg, 54.4%) as a light brown solid: ES(+)-HRMS m/e calcd for C37H45NO8S2 (M+H)+ 696.2660, found 696.2658.

Provenance & Evidence