HCID 178451388, compound → sodium (6R,7R)-3-[[3-(2-amino-2-iminoethyl)sulfanyl-4-cyano-1,2-thiazol-5-yl]sulfanylmethyl]-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of sodium 7β-[2-(2-aminothiazol-4-yl) -(Z)-2-(tert-butoxycarbonylmethoxyimino)acetamido]-3-hydroxymethyl-3-cephem-4-carboxylate (554 mg) and 3-amidinomethylthio-4-cyano-5-mercaptoisothiazole (345 mg) in 7 ml of DMF was added 1.2 g of ethyl o-phenylenephosphate under stirring at -20° C. After stirring under ice-cooling for 2 hours, the reaction mixture was subjected to a column chromatography on silica gel (150 g), being washed with acetonitrile and eluted with acetonitrile/water (6:1). The eluate was concentrated. The resultant precipitate was collected by filtration and dissolved in 40 ml of trifluoroacetic acid under ice-cooling. The mixture was stirred at room temperature for an hour and distilled to remove the solvent. The residue was dissolved in a mixture of water and THF and then adjusted to pH 6 with an aqueous sodium hydrogencarbonate solution. The solution was washed with ethyl acetate, concentrated under reduced pressure and subjected to a column chromatography on XAD-II (150 ml), being washed with water and eluted with 20% aqueous ethanol. The eluate was concentrated under reduced pressure and lyophilized to give 363 mg of the title compound as a pale yellow powder.

Provenance & Evidence