Sodium Iodide → HCID 141558884, compound

Participants

Reaction Steps

14.2 g (14.7 mmol) of benzhydryl 7-[(Z)-2-(1-tertbutoxycarbonyl-1-cyclopropoxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate was dissolved in 280 ml of methylene chloride, and 2.98 g (14.7 mmol) of m-chloroperbenzoic acid was added thereto under cooling with ice. The mixture was stirred for 10 minutes. To the reaction solution, 60 ml of a 10% sodium thiosulfate aqueous solution was added. The aqueous solution was poured into a 5% sodium hydrogen carbonate aqueous solution, then extracted with methylene chloride and dried over anhydrous sodium sulfate. The residue obtained by the concentration under reduced pressure was dissolved in 300 ml of acetone, and then 4.4 g (29.4 mmol) of sodium iodide was added thereto at 0° C. The mixture was stirred at room temperature for 15 minutes. The reaction solution was washed with a sodium thiosulfate aqueous solution and with a saturated sodium chloride aqueous solution. Then the organic solvent layer was dried over anhydrous sodium sulfate. The residue obtained by the concentration under reduced pressure was subjected to silica gel flush column chromatography (ethyl acetate/n-hexane=1/2) to obtian 9.52 g (yield: 60%) of the above-identified compound.

Provenance & Evidence