Hydrochloric Acid → HCID 66671696, compound

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Reaction Steps

The compound (470 mg, 1.08 mmol) obtained in Example 77b was dissolved in a mixed solvent of ethanol (5 mL) and water (5 mL), a 1 N aqueous sodium hydroxide solution (1.62 mL, 1.62 mmol) was added, and the mixture was stirred at room temperature. After the reaction was completed, a 1 N aqueous hydrochloric acid solution was added, and then the mixture was extracted with dichloromethane (×3). The solvent was evaporated under reduced pressure, the resulting residue and 1-[2-(methylamino)ethyl]piperidin-4-yl biphenyl-2-ylcarbamate (346 mg, 0.981 mmol) were dissolved in dichloromethane (10 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (375 mg, 1.96 mmol) was added, and the mixture was stirred at room temperature for 14 hours. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with dichloromethane (×3). The resulting organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, then the residue was purified by NH silica gel column chromatography (elution solvents, hexane:ethyl acetate=9:1→1:1→0:1, v/v) and then by silica gel column chromatography (elution solvents, ethyl acetate:methanol=10:0→9:1, v/v) to give the title compound (298 mg; yield, 41%) as a white solid.

Provenance & Evidence