Hydrochloric Acid → (6R,7R)-7-Amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Participants

Reaction Steps

To a slurry of 3.7 g (10 mmol) of p-nitrobenzyl 7β-amino-3-chloro-3-cephem-4-carboxylate and 61 ml of tetrahydrofuran, was added 8.03 g (60 mmol) of lithium iodide. The resulting reaction mixture was then heated to reflux and allowed to react for about 21/2 hours. The solution was cooled to complete the precipitation of lithium 7β-amino-3-chloro-3-cephem-4-carboxylate. This precipitate was isolated by filtration, slurried in 25 ml of tetrahydrofuran and then acidified to a pH of 3.7 with 1N hydrochloric acid resulting in the formation of a light solid. This solid was isolated by filtration and washed with a 25:3 tetrahydrofuran/water solution to provide 0.59 g of the desired titled product.

Provenance & Evidence