Protocatechuic Acid → HCID 22855045, compound

Participants

Reaction Steps

(6R,7R)-7-Amino-3-[[[2-(hydroxymethyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (4.08 g) (known from EPOS 302,633) and 1.54 g of 3,4-dihydroxybenzoic acid are treated with 30 ml of a 20% solution of boron trifluoride in acetonitrile and stirred at room temperature for 2 hours. A further 25 ml of a 20% solution of boron trifluoride in acetonitrile are added; the reaction mixture is stirred at room temperature under argon for 2 days. After the addition of 100 ml of ice-water the reaction mixture is concentrated to about half. The product is precipitated by adjusting the pH value to 2.0 with concentrated aqueous ammonia. The precipitated material is suspended in water, brought into solution with 1N aqueous sodium hydroxide solution and purified by chromatography on RP12-Kieselgel with water/acetonitrile. The product fractions are concentrated to about 50 ml and the product is precipitated by acidification to pH 2.0. After drying in a high vacuum there are obtained 1.60 g of (6R,7R)-7-amino-3-[[[2-[[(3,4-dihydroxybenzoyl)oxy]methyl]-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a white powder.

Provenance & Evidence