Methanesulfonic Acid → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(5-hydroxy-6-oxo-1H-pyrimidin-2-yl)methoxyimino]acetyl]amino]-3-[[5-(3,4-dihydroxyphenyl)-2-phenylpyrimidin-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-(3,4-dihydroxyphenyl)-2-phenyl-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (60 mg) (0.09 mmol), 20.5 mg (0.13 mmol) of 2-(aminooxy)methyl-5-hydroxy-4(1H)-pyrimidinone and 13 mg (0.13 mmol) of methanesulphonic acid are dissolved in 0.6 ml of absolute dimethylacetamide. After stirring at room temperature for 18 hours the mixture is concentrated in a high vacuum at room temperature and the residue is crystallized using ethanol. The product is washed with diethyl ether and dried in a high vacuum at room temperature. There are obtained 26 mg of (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[(1,4-dihydro-5-hydroxy-4-oxo-2-pyrimidinyl)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 yellow powder. A further 28 mg of yellow crystals of the same compound can be obtained from the mother liquor after concentration.

Provenance & Evidence