Pyridine → Doxorubicin

Participants

Reaction Steps

The compound obtained in Example <1-1> (55 mg, 0.0168 mmol) and p-nitrophenylchloromate (94 mg, 0.047 mmol) were dissolved in 4 ml of dichloromethane, and pyridine (68 μl, 0.084 mmol) was added thereto, followed by stirring the mixture at room temperature for 2 days. After the reaction was completed, the reaction mixture was dried in a vacuum oven to remove the solvent and dissolved in N,N-dimethylformamide (3 ml), and triethylamine (14.2 μl, 0.1 mmol) and doxorubicin-hydrochloride (13.7 mg, 0.0235 mmol; Waco Pure Chemical Industries, Ltd.) were added thereto, followed the darkroom treatment of the resulting mixture with stirring at room temperature for 1 day. The resulting solution was concentrated, and the residue thus obtained was purified by column chromatography (dichloromethane:methanol=10:1), to obtain the title compound as a red sticky solid (40.5 mg).

Provenance & Evidence