Chlorine → Benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-chloromethyl-3-butenate

Participants

Reaction Steps

1.0 g quantity of benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-methyl-3-butenate was dissolved in 10 ml of a benzenedioxane (1:2) mixture. To the solution was added 3 g of NaHCO3 and the mixture was stirred at room temperature. Thereto was added dropwise over 3 minutes 1.5 ml of carbon tetrachloride having dissolved therein 2.1 mmol of chlorine and the mixture was stirred for 2 hours. The reaction mixture was extracted with ethyl acetate and the extract was subjected to the same subsequent procedure as in Example 1, affording 1.04 g of benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-chloromethyl-3-butenate in 98% yield.

Provenance & Evidence