Hydrochloric Acid → HCID 14230833, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl 7-phenoxyacetamido-8-oxo-3-trifluoromethanesulfonyl-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylate (2.19 g.) and anisole (6.3 ml.) in methylene chloride (20 ml.) was added a solution of alminum trichloride (2.6 g.) in nitromethane (10 ml.) at 0° C. over a period of 5 minutes. The resultant deep red solution was stirred at 0° C. for 30 minutes. After the reaction mixture was poured into a mixture of ice and ethyl acetate (120 ml.), it was acidified to pH 1 with 3N hydrochloric acid. The organic layer was separated, washed twice with an aqueous solution of sodium chloride and hydrochloric acid and then extracted with a chilled dilute aqueous solution of sodium bicarbonate (once with 50 ml. and twice with 30 ml.). These aqueous extracts were combined, acidified to pH 1 with 3N hydrochloric acid, saturated with sodium chloride and then extracted three times with chloroform. Drying over magnesium sulfate and removal of the solvent afforded an amorphous solid (1.75 g.) of 7-phenoxyacetamido-8-oxo-3-trifluoromethanesulfonyl-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylic acid.

Provenance & Evidence