Trifluoroacetic acid → 2-(2-Hydroxy-5-(thiomorpholin-4-yl)benzamido)-4-phenylbenzoic acid

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Reaction Steps

Thioanisole (1.0 mL) was added to a trifluoroacetic acid (2.0 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-(thiomorpholin-4-yl)benzamido)-4-phenylbenzoate (0.10 g), followed by stirring at room temperature for 24 hours. The solvent was evaporated under reduced pressure, and a 4 mol/L hydrogen chloride-dioxane solution (0.5 mL) and ethyl acetate (1.0 mL) were added to the residue, followed by stirring at room temperature for 3 hours. The solid substance was collected by filtration, and water and ethyl acetate were added to the obtained solid substance. After adjusting the pH to 6.5 with a saturated aqueous solution of sodium bicarbonate, the organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: chloroform] to obtain 0.047 g of 2-(2-hydroxy-5-(thiomorpholin-4-yl)benzamido)-4-phenylbenzoic acid as a yellow solid.

Provenance & Evidence