Abstract
A simple procedure was devised for derivatization of the second carboxyl group in the molecule of dicarboxylic amino acids converted to 2,2-bis(chlorodifluoromethyl)-1,3-oxazolidinones in a preceding reaction stage. After condensation of the amino acids with 1,3-dichlorotetrafluoroacetone under catalytic influence of pyridine, the ketone was treated with a small amount of methanol, and the immediately formed halogenated alcohol esterified the second carboxyl group after a reactive anhydride such as heptafluorobutyric anhydride or trifluoroacetic anhydride was added. Factors influencing the reaction yields of a homologous series of dicarboxylic amino acids, with four to seven atoms, were studied and the possible side-product pathways discussed. A simple extraction procedure was devised to obtain the derivatives free of reactants in organic solvent. Molar responses relative to phenylamine (internal standard) are given and the gas chromatographic analysis on a methyl silicone phase is demonstrated.
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