Water → p-Nitrobenzyl 2-(3-phenylacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-chloromethyl-3-butenate

Participants

Reaction Steps

A 1.0 g quantity of p-nitrobenzyl 2-(3-phenylacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-methyl-3-butenate was dissolved in 25 ml of ethoxyethyl acetate. The solution was cooled in an ice bath with stirring. To the mixture was added dropwise over 20 minutes 6.l ml of a 0.285M solution of Cl2O in carbon tetrachloride. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was distilled off at reduced pressure. The resulting residue was separated and purified by silica gel column chromatography, giving 955 mg of p-nitrobenzyl 2-(3-phenylacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-chloromethyl-3-butenate in 90% yield.

Provenance & Evidence