Thioanisole → Methyl 2-(2-hydroxy-5-(2-(thiomorpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoate

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Reaction Steps

Thioanisole (3.2 mL) and trifluoroacetic acid (10 mL) were added to the obtained methyl 2-(2-(benzyloxy)-5-(2-(thiomorpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoate (0.80 g), followed by stirring at room temperature for 18 hours. The solvent was evaporated under reduced pressure, and a saturated aqueous solution of sodium bicarbonate and chloroform were added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 70-0% hexane/ethyl acetate to 100-95% chloroform/methanol] to obtain 0.54 g of methyl 2-(2-hydroxy-5-(2-(thiomorpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoate as a brown solid.

Provenance & Evidence