O-[(4-fluoro-2,2-diphenyl-1,3-benzodioxol-5-yl)methyl]hydroxylamine hydrochloride → 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)-2-phenyl-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (66 mg) (0.1 mmol) and 47 mg (0.13 mmol) of O-[(4-fluoro-2,2-diphenyl-1,3-benzodioxol-5-yl)methyl]hydroxylamine hydrochloride are dissolved in 1 ml of absolute of dimethylacetamide. After stirring at room temperature for 20 hours the mixture is concentrated in a high vacuum at room temperature and the residue is treated with 0.45 ml of ethanol and 3 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 98 mg of (6R,7R)-7-[(Z)-2(2-amino-4-thiazolyl)-2-[[(4-fluoro-2,2-diphenyl-1,3-benzodioxol-5-yl)methoxy]imino]acetamido]-3-[[5-(3,4-dihydroxyphenyl)-2-phenyl-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