Lipoic acid → HCID 131731047, compound

Participants

Reaction Steps

Paclitaxel-lipoate was synthesized from paclitaxel (Farmachem, Lugano, Switzerland) and lipoic acid (Sigma, St. Louis, Mo., USA) in a single step that coupled lipoate to paclitaxel at the 2′-hydroxyl position. To a solution of paclitaxel (35 mg; 41 μmmol) in dry methylene chloride (2.5 ml) under nitrogen were added 4-dimethylaminopyridine (5 mg; 41 μmmol), 1, 3-dicyclohexylcarbodiimide (16.9 mg; 82 μmmol), and lipoic acid (8.5 mg; 41 μmol). The reaction mixture was stirred at ambient temperature for 2 h. After dilution with diethyl ether, the reaction mixture was washed with 5% aqueous hydrochloric acid, water, and saturated aqueous sodium chloride. The mixture was dried (sodium sulfate) and concentrated. Radial chromatography (silica gel; ethyl acetate-hexane 1:1) of the residue gave 45 mg (90%) of solid paclitaxel-lipoate. The product was analysed using LC-MS as shown in FIG. 3 and H-NMR as shown in FIG. 4.

Provenance & Evidence