2-[(aminooxy)methyl]-5-hydroxy-4H-pyran-4-one p-toluenesulphonate → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(5-hydroxy-4-oxopyran-2-yl)methoxyimino]acetyl]amino]-3-[[5-(3,4-dihydroxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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Reaction Steps

(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[5-(3,4-dihydroxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (59 mg) (0.095 mmol) and 41 mg (0.121 mmol) of 2-[(aminooxy)methyl]-5-hydroxy-4H-pyran-4-one p-toluenesulphonate (1:1) are dissolved in 2 ml of absolute dimethylaeetamide. After stirring at room temperature for 24 hours the solvent is removed and the residue is treated with 4 ml of water. The precipitated product is filtered off and washed with water. After drying in a high vacuum at room temperature there are obtained 67 mg of (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[(5-hydroxy-4-oxo-4 H-pyran-2-yl)methoxy]imino]acetamido]-3-[[[5-(3,4-dihydroxyphenyl)pyrazolo[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 yellow powder.

Provenance & Evidence