Citric Acid → HCID 58508951, compound

Participants

Reaction Conditions

Reaction Steps

A 1 mol/L aqueous solution of sodium hydroxide (0.17 mL) was added to a solution mixture of the obtained tert-butyl 2-(2-hydroxy-5-(piperidin-1-yl)benzamido)-4-(thiophen-2-yl)benzoate (0.027 g) in dioxane (2.0 mL) and methanol (2.0 mL), followed by stirring at 50 to 55° C. for 1 hour. The reaction mixture was cooled to room temperature, and a 1 mol/L aqueous solution of sodium hydroxide (0.11 mL) was added thereto, followed by stirring at 50 to 55° C. for 2 hours. The reaction mixture was cooled to room temperature, and a 1 mol/L aqueous solution of sodium hydroxide (0.056 mL) was added thereto, followed by stirring at 55° C. for 1 hour. The reaction mixture was cooled to room temperature, and a 1 mol/L aqueous solution of sodium hydroxide (0.056 mL) was added thereto, followed by stirring at 60° C. for 2 hours. The reaction mixture was cooled to room temperature and then adjusted to a pH of 7.7 with a 10% aqueous solution of citric acid, and water and ethyl acetate were added thereto. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, and the resulting mixture was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-80% chloroform/methanol] to obtain 0.011 g of 2-(2-hydroxy-5-(piperidin-1-yl)benzamido)-4-(thiophen-2-yl)benzoic acid as an orange solid.

Provenance & Evidence