A Study On Asymmetric Synthesis Of (S)-isoserine

With the development of the asymmetric synthesis, the study of chiral drug is to advance rapidly. The magnitude market demand causes the chiral durg to become industrially developed from the laboratory.β-amino acid is a chiral intermediate which draws more attention recently. It has been successively used in various applications such as medicament and artificial synthesis of peptide. (S)-isoserine is an importantα-hydroxyl-β-amino acid and important pharmaceutical intermediate. Various processes for synthesis of (S)-isoserine are introduced. In this paper, (S)-isoserine is synthesized by the technique of asymmetric catalysis. First of all, the Jacobsen catalyst was obtained, its structure was characterized by IR, 1H NMR, 13C NMR. And then, optical active (S)-methyl glycidate was got by hydrolytic kinetic resolution of terminal epoxide by the Jacobsen catalyst. Systematic studying the reaction temperature, ligand and concentrations of catalyst was to get the optimum conditions. At last, amino group was added by Gabriel reaction. The final production was obtained by hydrolysis and hydrazinolysis using HCl and hydrazine hydrate. IR, 1H NMR, 13C NMR,MS, Elementary Analysis and polarimeter were used to characterize the structure of the product.It turned out that high optical active (S)-isoserine was got by the technique of asymmetric catalysis. The synthetic route has the advantages of convenient, safety, low cost and was suitable for scale-up production.