Boron trifluoride → HCID 131709915, compound

Participants

Reaction Conditions

Reaction Steps

0.1 g of 3-acetoxymethyl-7-(N-phenylacetyl-amino)-ceph-2-em-4ξ-carboxylic acid are dissolved in a solution of 0.056 g of anisole in 5 ml of chloroform, and the solution is cooled to 0°C and saturated with boron trifluoride gas for 15 minutes. The temperature of the reaction mixture is thereafter brought to room temperature over the course of 2 hours; 50 ml of acetic acid ethyl ester are added, and the mixture is again cooled to 0°C and slowly poured into 50 ml of a 10% strength aqueous dipotassium hydrogen phosphate solution. The pH value is adjusted to 7.5 and the mixture is thoroughly shaken. The aqueous phase is twice washed with 50 ml portions of acetic acid ethyl ester, the pH value is adjusted to 2 by means of 20% strength aqueous phosphoric acid, and three extractions with 50 ml portions of acetic acid ethyl ester are carried out. The oroganic extracts are repeatedly washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure. 3-(4-Methoxy-benzyl)-7-(N-phenylacetyl-amino)-ceph-2-em-4ξ-carboxylic acid containing a small amount of the corresponding 2-methoxy-benzyl compound are thus obtained as the residue; in a thin layer chromatogram, this acid does not differ from the product of the process of example 1.

Provenance & Evidence