Anisole → HCID 13938971, compound

Participants

Reaction Conditions

Reaction Steps

54.5 g (0.123 mol of benzhydryl 7-amino-3-[(Z)-1-propen-1-yl]-3-cephem-4-carboxylate (Example 10) are added to a stirred solution of 500 ml of trifluoroacetic acid (TFA) and 31 ml of anisole, which is cooled to 0° C. The mixture is stirred at room temperature for 1 hour and is then concentrated in vacuo at 30° C. and the oily residue is stirred with 600 ml of ether for 1 hour. The precipitate is filtered off with suction and washed with 300 to 400 ml of ether and the residue on the filter is dried in vacuo for 3 hours. The trifluoroacetate is suspended in 300 ml of water, the suspension is cooled to +5° C. and the pH is brought to 0.2-0.4 with 12N HCl. The resulting clear solution is cooled to +5° C. and stirred with 4 g of active charcoal for 10 minutes. The active charcoal is filtered off with suction over kieselguhr and rinsed with about 50 ml of 0.1N HCl. The filtrate is brought to pH 2.1 at +5° C. with 20% strength NaOH and the product which has precipitated out is left to stand in a refrigerator for 1 hour in order to bring the crystallization to completion. The crystal sludge is filtered off with suction, washed with 100 ml of water and 300 ml of acetone and dried in vacuo.

Provenance & Evidence