Dicyclohexylcarbodiimide → benzhydryl (6R)-3-[(Z)-2-(4-methylthiadiazol-5-yl)ethenyl]-8-oxo-7-[[(2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetic acid (1.58 g, 2.35 mmol) was dissolved in a mixed solvent of THF-methylene chloride (20 ml-10 ml) and cooled to 5° C. HOBT (0.32 g, 2.4 mmol) was added to this reaction solution, then DCC (0.50 g, 2.4 mmol) was added and the mixture was stirred at the same temperature for 2 hours. The reaction solution was filtered, then benzhydryl 7-amino-3-[(Z)-2-(4-methyl-1,2,3-thiadiazol-5-yl)vinyl]-3-cephem-4-carboxylate (0.98 g, 2.0 mmol) was added to the filtrate and it was stirred at 5° C. for 22 hours. The reaction solution was concentrated and then the concentrate was purified by column chromatography thereby benzhydryl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(Z)-2-(4-methyl-1,2,3-thiadiazol-5-yl)vinyl]-3-cephem-4-carboxylate (1.38 g, 60.5% yield) was obtained as a yellow powdered compound.

Provenance & Evidence