2,2-Dimethyl-5-(3-thienyl)-1,3-dioxane-4,6-dione → HCID 178477386, compound

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Reaction Steps

To a suspension of 656.7 mg (2 mmol) of 7-amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (as prepared in example 9) in 25 ml. of anhydrous tetrahydrofuran there is added 1.6 ml. of bis-trimethylsilylacetamide. The mixture is stirred to give a solution to which there is added at once 452.5 mg (2 mmol) of 2.2-dimethyl-5-(3-thienyl)-1.3-dioxane-4.6-dione as prepared in example 6, the mixture being stirred at 25° C for 8 hours. Tetrahydrofuran is removed under reduced pressure and the residue is taken up with 30 ml. of water, brought to pH 2.5 with 0.5 ml. 6N HCl, stirred for 15 minutes and extracted three times with 25 ml. of ethyl acetate. The organic layer is dried over anhydrous sodium sulfate and filtered over DARCO G60 (a product manufactured and sold by Atlas Chem. Ind.)-charcoal. Most of the solvent is evaporated under reduced pressure and 100 ml. of petroleum ether (50°-70° C) is added thereto. The suspension is stirred for 30 minutes and filtered. The precipitate is washed with 20 ml. of petroleum ether (50°-70° C) and dried over anhydrous P2O5 under reduced pressure to yield DL-7-[α-carboxy-α-(3-thienyl)-acetamido]-3-(1-methyl-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (RIT 3838).

Provenance & Evidence