Boron trifluoride etherate → (6R,7R)-7-Amino-3-[[[5-(3,4-dihydroxyphenyl)-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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Reaction Steps

7-Aminocephalosporanic acid (220 mg) (0.81 mmol) and 250 mg (1.04 mmol) of 5-(3,4-dihydroxyphenyl)-4(3H)-pyrimidinethione are suspended in 8 ml of sulpholane/dichloromethane (1:1 v/v) and treated with 5 ml of boron trifluoride diethyl etherate while stirring. After 18 hours the mixture is concentrated in a vacuum and the residue is washed with diethyl ether. Then, 2 ml of ethanol and 4 ml of water are added thereto and sodium hydrogen carbonate is added until pH 5 has been reached. The product is filtered off under suction, washed with water and diethyl ether and dried in a high vacuum at room temperature. There are obtained 311 mg of (6R,7R)-7-amino-3-[[[5-(3,4-dihydroxyphenyl)-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a beige powder.

Provenance & Evidence