Hydrochloric Acid → HCID 23147014, compound

Participants

Reaction Steps

Compound 116 obtained in Example 116 was dissolved in tetrahydrofuran (10 mL), and triethylamine (0.35 mL, 2.5 mmol) and methyl chlorocarbonate (0.18 mL, 2.3 mmol) were added thereto and stirred at room temperature for 1 hour. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in tetrahydrofuran (10 mL), and under stirring with ice-cooling, aqueous solution (5 mL) of sodium borohydride (150 mg, 4.0 mmol) was dropwise added thereto, and stirred for 1 hour. Water was added to the reaction solution, and extracted twice with ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through silica gel column chromatography (ethyl acetate/n-hexane 1/1) to obtain a crude product. Methanol solution (10 mL) of 7 mol/L hydrochloric acid was added to the resulting crude product, and stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (ethyl acetate/n-hexane=1/4 to 1/1) to obtain Compound 118 (53 mg, 18%)

Provenance & Evidence