Ethanol → HCID 86609024, compound

Participants

Reaction Steps

Ethanol (5.0 mL) and tetrahydrofuran (2.0 mL) were added to the compound obtained in Example 367 (270 mg) for dissoltion, and hydroxylamine hydrochloride (114 mg) and triethylamine (230 μL) were added to the solution at room temperature. The mixture was heated under reflux for 3 hours, and saturated aqueous sodium hydrogencarbonate and methylene chloride were added to the reaction mixture to partition the mixture, followed by extracting the formed aqueous layer with methylene chloride. The extract was combined with the organic layer, and the mixture was dried over sodium sulfate anhydrate. The solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography (methylene chloride:methanol=7:1), a sephadex column (methanol), and fractional reversed phase high performance liquid chromatography (acetonitrile-water-formic acid). The product was converted to a hydrochloride with 1N HCl, and subsequently, the salt was purified through use of a sephadex column (methanol), to thereby yield the title compound (175 mg) as a white solid.

Provenance & Evidence