Dichloromethane → (6R,7R)-7-amino-3-[[[2-(N-hydroxy-N-methylcarbamoyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4,2,01oct-2-ene-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

N-Hydroxy-7-mercapto-N,5-dimethyl-s-triazolo[1,5-a]pyrimidine-2-carboxamide (53 mg) (0.22 mmol) and 54 mg (0.2 mmol) of 7-aminocephalosporanic acid are suspended in 1 ml of dichloromethane/sulpholane (1:1 v/v). 0.5 ml of boron trifluoride diethyl etherate is added thereto at 10° C. while stirring and the mixture is stirred at room temperature for a further 20 hours. Subsequently, about 10 ml of dichloromethane are added thereto, the insoluble material is filtered off under suction, dissolved in water and the product is precipitated by the addition of sodium hydrogen carbonate (pH→4). The precipitate is filtered off under suction and washed with water and ethanol. There are obtained 66 mg of (6R,7R)-7-amino-3-[[[2-(N-hydroxy-N-methylcarbamoyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4,2,01oct-2-ene-2-carboxylic acid as a white powder.

Provenance & Evidence