We present the synthesis of a peptide-based chiral ionic liquid (CIL) derived from an α-L-aspartyl-L-phenylalanine methyl ester (aspartame) cation and bis(trifluoroethyl)sulfonyl imide anion. A hydrochloride salt of α-L-aspartyl-L-phenylalanine methyl ester was prepared by dissolving α-L-aspartyl-L-phenylalanine methyl ester in a solvent composed of a mixture of methanol and hydrochloric acid and allowing the solution to sit at room temperature to crystallize out the salt. The isolated α-L-aspartyl-L-phenylalanine methyl ester hydrochloride was used to prepare α-L-aspartyl-L-phenylalanine methyl ester bis(trifluoroethyl)sulfonyl imide ionic liquid through an ion-exchange reaction with the lithium salt of bis(trifluoroethyl)sulfonyl imide. This was achieved by mixing equimolar aqueous separate solutions of the anion and cation and stirring the mixture for several days at room temperature until all the water evaporated off. The purity of the ionic liquid is being evaluated using both proton and carbon NMR and the physical chemical properties such as viscosity, melting point and thermal stability as well as the chiral recognition ability of the ionic liquid are being investigated.

Synthesis and evaluation of a chiral ionic liquid derived from an aspartame cation for potential applications in chromatographic separations

2019 Spring National Meeting

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