Cyclohexanecarboxylic acid → HCID 86737467, compound

Participants

Reaction Steps

In 5 ml of dry dichloromethane are dissolved maytansinol (103.2 mg, 0.183 mmol) and cyclohexanecarboxylic acid (140 mg, 1.094 mmols), followed by addition of dicyclohexylcarbodiimide (DCC) (267 mg, 1.296 mmols). The mixture is stirred at room temperature for a while until insolubles have begun to separate out. Then, after addition of p-dimethylaminopyridine (DMAP) (50.8 mg, 0.416 mmol), the reaction mixture is stirred at room temperature overnight. The insolubles are filtered off, the filtrate is washed with 0.5 N HCl (ca. 10 ml) and saturated aqueous sodium hydrogen carbonate (ca. 10 ml) in that order and dried over anhydrous sodium sulfate. After the solvent is distilled off, the residue is chromatographed on a column of silica gel (75 g) and elution is carried out with ethyl acetate, the eluate being collected in 16-g fractions. Fractions 14 through 30 are pooled and the solvent is distilled off to recover 59 mg of crude product. This crude product is dissolved in ethyl acetate, followed by addition of ether, whereby 24.3 mg of maytansinol 3-cyclohexanecarboxylate is obtained as crystals melting at 202°-206° C. (decompn.)

Provenance & Evidence