Sodium Hydroxide → HCID 59529523, compound

Participants

Reaction Steps

To a mixture of 5-{[cyclohexyl(2-methyl-5-phenylthiophen-3-yl)methyl]amino}pyridine-2-carboxylic acid (386 mg) synthesized above, ethyl β-alaninate hydrochloride (218 mg), 1-hydroxybenzotriazole monohydrate (218 mg), triethylamine (397 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (272 mg), and the mixture was stirred at room temperature overnight. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (30-50% ethyl acetate/hexane) to give a white solid. To a mixture of the obtained solid, tetrahydrofuran (5 mL) and ethanol (5 mL) was added 1N aqueous sodium hydroxide solution (2.00 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in water (10 mL), and 1N hydrochloric acid (2.00 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title compound (311 mg, 69%) as a white solid.

Provenance & Evidence