2-(aminooxy)-N-hydroxy-2-methylpropionamide hydrochloride → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[1-(hydroxyamino)-2-methyl-1-oxopropan-2-yl]oxyiminoacetyl]amino]-3-[[5-(3,4-dihydroxyphenyl)pyrimidin-4-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-(3,4dihydroxyphenyl)-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (90 mg) (0.15 mmol) and 34 mg (0.2 mmol) of 2-(aminooxy)-N-hydroxy-2-methylpropionamide hydrochloride are dissolved in 2 ml of absolute dimethylacetamide. After stirring at room temperature for 24 hours the mixture is concentrated in a high vacuum at room temperature and the residue is crystallized from ethanol/diethyl ether. It is filtered off under suction and washed with ether and water. After drying in a high vacuum at room temperature there are obtained 72 mg of (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-(hydroxycarbamoyl)-1-methylethoxy]imino]acetamido]-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