Sodium Iodide → HCID 14621643, compound

Participants

Reaction Steps

14.5 g (36.6 mM) of p-methoxybenzyl 3-chloromethyl-7-formamido-3-cephem-4-carboxylate was dissolved in 360 ml of acetone. Under cooling with ice, 13.7 g (91.4 mM) of sodium iodide was added to this solution, and the mixture was stirred for 30 minutes, and further at room temperature for 30 minutes. The reaction solution was concentrated under reduced pressure, and the oily residue was dissolved by an addition of ethyl acetate. The organic layer was washed sequentially with water, a saturated sodium thiosulfate aqueous solution and a saturated sodium chloride aqueous solution. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The oily residue was subjected to silica gel column chromatography (Wakogel C-300, eluted with 20% ethyl acetate-chloroform), and the fraction containing the desired product was concentrated to obtain 15.7 g (yield: 87.9%) of p-methoxybenzyl 7-formamido-3-iodomethyl-3-cephem-4-carboxylate.

Provenance & Evidence