4-[[(Aminooxy)-methyl]sulphonyl]pyrocatechol hydrochloride → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(3,4-dihydroxyphenyl)sulfonylmethoxyimino]acetyl]amino]-3-[[2-(hydroxycarbamoyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Participants

Reaction Steps

(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[2-(hydroxycarbamoyl)-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 (80 mg) (0.135 mmol) and 45 mg (0.176 mmol) of 4-[[(aminooxy)-methyl]sulphonyl]pyrocatechol hydrochloride are dissolved in 4 ml of absolute dimethyl-acetamide. After stirring at room temperature for 24 hours a further 14 mg (0.06 mmol) of 4-[[(aminooxy)-methyl]sulphonyl]-pyrocatechol hydrochloride are added. After a further 24 hours the solvent is removed in a high vacuum at room temperature and the residue is treated with 4 ml of water. The precipitated product is filtered off under suction and washed in succession with water and diethyl ether. There are obtained 100 mg of (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[[(3,4-dihydroxyphenyl)sulphonyl]methoxy]imino]acetamido]-3-[[[2-(hydroxy-carbamoyl)-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 brown powder.

Provenance & Evidence