Sodium Hydroxide → benzhydryl (6R,7R)-7-[[(2Z)-2-acetyloxyimino-2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-8-oxo-3-(pyridin-4-ylmethylsulfanyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

Diphenylmethyl 7β-amino-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylate (2.15 g, 4.39 m mol) was dissolved in dichloromethane (50 ml) by addition of bis(trimethylsilyl)acetamide (1.79 g, 8.78 m mol). To a resulting solution was added 2-(2-aminothiazol-4-yl)-2-(Z)-(acetoxyimino)acetyl chloride hydrochloride (1.50 g, 5.27 m mol) at 5° C. and the mixture was stirred at 5° C. for 1.5 hours and at room temperature for 16 hours. The mixture was poured into a mixture of water and methanol and adjusted to pH 7 by addition of 1N NaOH aq. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated in vacuo to give diphenylmethyl 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(acetoxyimino)acetamido]-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylate (2.37 g).

Provenance & Evidence