Cephalosporins Cefuroxime Intermediate Synthesis And Antibacterial Activity

A new route for preparation of 2-methoxyimino-2- furyl acetic acid was brought forward in this paper. The preparation ofα-methoxy acetic acid was also discussed. The reaction tolerated a series of substitution patterns, including aryl-, acyclic- and heterocyclic- substitution compounds. The antibacterial action of methyl 2-methoxy-2-furan-acetate was studied.(1) The synthetic craftwork of 2-methoxyimino-2- furylacetic acid including three reaction steps was confirmed. The first step was the preparation of the condensation product by the aldol condensation from 2-acetoxytetrahydrofuran and benzophenone at 30°C for half an hour by using sodium hydroxide and sodium carbonate as pH modifying addition at pH value of 9. The second step was the oxidation of the condensation product with potassium permanganate to prepare 2-furanyloxoacetic acid in presence of 40% sodium hydroxide for about 8 hours. At last, the third step was the preparation of 2-methoxyimino-2- furylacetic acid by oximation from 2-furyloxoacetic acid and methoxylaminehydrochloride. The molar ratio of the two reactants was 1:1.2, the temperature of the reaction was 40°C and the pH of the medium was about 5-6. The production was buff crystal and the melting point was 87-89°C. The results of ~1HNMR and IR spectrum show that the synthesized product accords with the target.(2) The synthetic craftwork of a series ofα-methoxy acids was confirmed, thereinto the material aldehydes including benzophenone furfural, isobutyraldehyde, 2-methoxybenzaldhyde. Trichloromethyl car-binols were the important intermediates for synthesis ofα-methoxy acids. Trichloromethyl carbinols were obtained from 50% aqueous sodium hydroxide to one equivalent of aldehyde and two equivalent of chloroform stirred for 4h at 0-5°C by adding tetrabuthylammonium chloride as a phase transfer catalyst. Methoxy ion was used as the nucleophilic reagent to obtainα-methoxy acid. The results of ~1HNMR spectrum show that the synthesized furyl- compounds accords with the target. (3)The antimicrobial activity of methyl a-methoxy-2-furanacetate was examined, which have not been reported previous. The experiment show that its minimum inhibition concentration was 0.40g/L for Candida albicans, 0.50g/L for Staphylococcus aureus, 0.60g/L for Bacillus subtilis. These showed that methyl a-methoxy-2-furanacetate could inhibit bacteria and fungal effectively.