Synthesis And Their Resolution Ability Evaluation Of Poly(Meth)Acrylamides Chiral Stationary Phase

The evolution of chiral separation will promote the developing process of chiraldrugs, and also provide effective analytical means of researching chiral drug. In recentyears, the proportion of amino acid derivatives chiral drugs had increased rapidly,which were synthetized with amino acids. In consideration of the obvious separatingability of Amides chiral stationary phase who used amino acids as raw material, ithad broad application prospects which contain the study of chiral drugs anddevelopment of chiral technology.Using chiral L-phenylglycine and L-phenylalanine as raw materials, a new chiralmonomer L-ACBMAM and L–ACBEMAM were synthetized through two stepamidation reaction.The target product whose purity exceeded95%was achievedusing nuclear magnetic resonance (NMR) as analytical tools.Methyl acrylamide PACBMAM and PACBEMAM which has different tacticitywas synthetized by the free radical polymerization, the Optical rotation andmolecular weight distribution of PACBMAM and PACBEMAM was observedunder the condition of lewis acid appeared in the process of radical polymerization.The results showed that the tacticity and the molecular weight of polymer can beimproved or controlled when Lewis acid existed.The coating or bond type chiral stationary phase(CSP) of poly(meth)acrylamideswas analysed by thermogravimetric analyzer (TGA); Optical activity of this two kindsof polymer in different solvents was researched by CD spectra and polariscope, andthe results indicated that there were a lot of differences in optical rotation when thepolymer dissolved in different solvent.The chiral stationary phase was prepared by the coating methods, which is“glued” to the surface of silica gel using two kinds of polymer.12enantiomers wassplited by the chiral stationary phase in HPLC. Then, we observed the influences ofdifferent mobile phase matching, diverse coating solvent on CSPs chiral recognitionability. The CSPs used PACBMAM as raw material have split effect on9enantiomerscommonly, the CSPs used PACBEMAM as raw material have split effect on5enantiomers commonly; the chiral recognition ability of CSP polymer when Lewisacid didn’t exist in the process of polymerization is better than with it; The best test mobile phase is H/C/I=89/10/1(v/v/v) and H/C/I=85/14/1(v/v/v); when usingchloroform as coating solvent, the chiral recognition ability of CSP is better thanusing THF as coating solvent.The bond type chiral stationary phase were prepared by the copolymerizationmethod,which means that the monomer L-ACBMAM and L-ACBEMAM wereboned respectively with the ammonia propyl silica gel. And we researched theinfluence of HPLC testing conditions on the CSP chiral recognition ability. Theresults showed that H/C/I=85/14/1(v/v/v) is the best when testing bond type CSP;and the chiral separating effect of bond type CSP wasn’t as good as the coating typeCSP.