Synthesis And Chiral Separation Of β-amino Acids

β-amino acids scarcely exist in nature butβ-amino acids and the compouds containedβ-amino acids show unique pharmacological properties. Usually,β-amino acids utilize as optically pure form in application so we make our efforts to obtain theβ-amino acids enantiomers. Modern chromatography techniques play important roles in separation of chiral compounds due to their fast, easy operating and low cost. Among these methods, CSP(chiral solid phase) have been used to separate amino acids and get excellent results. CLEC ( chiral ligand exchange ) and CCE ( chiral crown ether) are superior among them.In this thesis , we synthesized sixβ-amino acids racemates , five of them have benzene ring and the other one is thiophene-β-amino acid. During the process of synthesis,purification methods have been optimized and yield have been raised to some extent. Following procedures are separating them by CLEC and good results have been obtained with baseline separation(αbetween 1.14 and 2.70 )by optimization of chromatography conditions including centrual Cu2+concentration, methanol, flow rate and pH of mobile phase. But we found a question before preparingβ-amino acids enantiomers that the remove of Cu2+ is a indispensable procedure.So we synthesized (-)-(18-crown-6)- 2,3,11,12- tetracarboxylic acid with simple four-step reactions, tartaric acid as material. The following preparation of chiral crown ether solid phase is made by (-)-(18-crown-6)- 2,3,11,12-tetracarboxylic acid bonded with aminopropyl silica . During the chiral separation ofβ-amino acids which we synthesized before by chiral crown ether solid phase, three of them have good separation results(α=1.16,1.20,1.20). During the process of drug screening, we expect to establish a facile, effective method for preparation ofβ-amino acids enantiomers by synthesis and chiral separation ofβ-amino acids.