Sodium Hydroxide → N-{4-[2-(1-Hydroxyethyl)-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl}propanamide

Participants

Reaction Steps

An 1N aqueous sodium hydroxide solution was added dropwise to a solution of 1-[4-(3-methylphenyl)-5-(2-propionylamino-4-pyridyl)-1,3-thiazol-2-yl]ethyl benzoate (1.63 g, 3.46 mmol) in methanol (5 mL) and tetrahydrofuran (20 mL) at 0° C. and the reaction mixture was allowed to warm up to room temperature. The resulting mixture was stirred at room temperature for 30 minutes and the solvent was removed under reduced pressure. The residue was treated with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extracts were washed with aqueous sodium hydrogen carbonate solution and brine. The resulting solution was dried, and concentrated under reduced pressure. The obtained crude crystal was recrystallized from ethyl acetate-hexane to give a title compound (1.12 g, yield 89%).

Provenance & Evidence