Diethyl Ether → HCID 86737467, compound

Participants

Reaction Steps

To a mixed solution of maytansinol (103.2 mg, 0.183 mmoles) and cyclohexanecarboxylic acid (140 mg, 1.094 mmoles) in 5 ml of dry dichloromethane is added dicyclohexylcarbodiimide (DCC) (267 mg, 1.296 mmoles), and after stirring at a room temperature for a short while until insolubles begin to separate out, p-dimethylaminopyridine (DMAP) (50.8 mg, 0.416 mmoles) is added. The mixture is stirred at a room temperature overnight. Then, the insolubles are filtered off, and the filtrate is washed with 0.5 N-HCl (ca. 10 ml) and with saturated aqueous sodium hydrogen carbonate (ca. 10 ml) in that order and is dried over anhydrous sodium sulfate. The solvent is distilled off, and the residue is chromatographed on a column of silica gel (75 g), followed by eluting with ethyl acetate and collecting the eluate in 16 g fractions. The fractions No. 14 through No. 30 are pooled and concentrated to remove the solvent, resulting in 59 mg of the crude product. The crude product is dissolved in ethyl acetate, followed by adding ether. There is obtained 24.3 mg of maytansinol 3-cyclohexanecarboxylate as crystals melting at 202°-206° C. (decomp.).

Provenance & Evidence