Study of the reaction of diazomethane with dansylated amino acid derivatives by gas chromatography/mass spectrometry

Since the methylation of acids with diazomethane is widely used in trace analysis, it is extremely important for those using this technique to be alert to the analysis of compounds containing other functional groups which might become methylated with high concentrations of diazomethane. We have shown that by adding an excess of diazomethane to dansylated amino acids, not only is the methyl ester formed, but the products can be further methylated. The only remaining acidic hydrogen in the molecule is the hydrogen attached to the sulfonamide nitrogen, and the mass spectrometry results indicate that the methyl ester is formed first, and the N-methylated derivative is formed with excess diazomethane.