Acetyl chloride → 2,2-dimethylpropanoyloxymethyl (6R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

The 1-oxide derivative (85 mg) from Example 4 was dissolved in dimethylformamide (2 ml, followed by addition of SnCl2.2H2O (84 mg) and cooling with ice. Acetyl chloride (0.38 ml) was added dropwise to the mixture. Then the ice bath was removed to raise the temperature to 20° C. After stirring for 15 minutes, the reaction mixture was added to cold water (10 ml). The mixture was extracted three times with ethyl acetate (15 ml×3). The ethyl acetate layers, combined together, were washed with water, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure. The residue was dissolved in ethyl acetate (0.5 ml) and the solution was added dropwise to petroleum ether (30 ml) with stirring. Resulting crystals were filtered, and dried under reduce pressure to give the title compound (35 mg).

Provenance & Evidence