Hydrochloric Acid → HCID 86609026, compound

Participants

Reaction Steps

Saturated HCl in ethanol (30 mL) was added to the compound obtained in Example 367 (300 mg) at room temperature. The mixture was stirred for 2 days and then concentrated under reduced pressure, thereby yielding a pale yellow solid. The solid was dissolved in methanol (10 mL). O-Methylhydroxylamine hydrochloride (1.01 g) and triethylamine (1.69 mL) were added to the solution at room temperature. The mixture was stirred for 2 hours, and methylene chloride and saturated aqueous sodium hydrogencarbonate were added to the reaction mixture to partition the mixture, followed by extracting the aqueous layer with methylene chloride. The extract was combined with the organic layer and then dried over sodium sulfate anhydrate, and the solvent was removed under reduced pressure. The residue was purified sequentially through silica gel medium-pressure chromatography (methylene chloride:methanol=20:1→7:1) and fractional reversed phase high performance liquid chromatography (acetonitrile-water-formic acid), and the product was treated with 1N HCl, to thereby yield the title compound (51.8 mg) as a white solid.

Provenance & Evidence