1,1'-(Diazomethylene)bis(benzene) → HCID 70636339, compound

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Reaction Steps

A solution of 0.39 g of diphenyldiazomethane in 5 ml of petroleum ether is added dropwise over the course of half an hour to a solution of 0.5 g of 3-methylthiomethyl-7β -phenylacetylamino-2-cephem-4α-carboxylic acid in 20 ml of dioxane, while stirring. The solution is stirred for a further 15 hours at room temperature, treated with a few drops of glacial acetic acid and concentrated under reduced pressure. The residue is recrystallised from methyl acetate and gives pure 3-methylthiomethyl-7β-phenylacetylamino-2-cephem-4α-carboxylic acid diphenylmethyl ester which is dried for 16 hours at room temperature in a high vacuum. Melting point 175-177° C; thin layer chromatogram (silica gel): Rf = 0.77 (system: chloroform/methanol, 1:1); Rf = 0.17 (system: toluene/acetone, 2:1); [α]D20 + 342° ± 1° (c = 1.011 in dioxane); ultraviolet absorption spectrum (in 95% strength aqueous ethanol): λmax = 255 mμ (ε = 7,800) and λmin = 244 mμ (ε = 7,200), infra-red absorption spectrum (in methylene chloride): characteristic bands at 2.92μ, 5.61μ, 5.73μ, 5.92μ, 6.25μ and 6.67μ.

Provenance & Evidence