Synthesis And Characterization Of The N-substituted Derivatives Of 5-oxo-pyrrolidine-2-carboxylic Acid

The heterocyclic compounds of N-substituted derivatives of pyrrolidine carboxylic acid (as know as proline) have attracted a great deal of attention of scientists in their studying and developing new drugs and pesticides because of their high selectivity and biological activity. In order to find new synthesized routes and improve the harvest, we have studied some basic principles and methods of synthesis.In this dissertation,α-ketoglutarate acid was reacted with (4-amino-phenyl)- acetic acid tert-butyl ester,(4-amino-phenoxy)-acetic acid tert-butyl ester, 3-(4-amino-phenyl)-propionic acid tert-butyl, 3-(3-amino-phenyl)-propionic acid tert-butyl ester, 3-(2-amino-phenyl)-propionic acid tert-butyl ester,using tert -butyl alcohol ast the solvent at room temperature, and N-(4-tert- Butoxycarbonylmethyl-phenyl)-5-oxo-pyrrolidine-2-carboxylicacid, N-(4-tert-Butox- ycarbonylmethoxy-phenyl)-5-oxo-pyrrolidine-2-carboxylicacid,N- [4-(2-tert-Butoxy- carbonyl-ethyl)-phenyl]-5-oxo-pyrrolidine-2-carboxylicacid,N-[3- (2-tert-Butoxycar- bonyl-ethyl)-phenyl]-5-oxo-pyrrolidine-2-carboxylicacid, N-[2-(2-tert-Butoxycarbon- yl-ethyl)-phenyl]-5-oxo-pyrrolidine-2-carboxylic acid, were obtained. All the synthesized compounds were purified by recrystallization or column chro-matography and were characterized by 1H NMR, IR. And some possible reaction mechanisms of have been discussed and provided.The results indicated that some synthesis methods have been optimized and better yields and convenient operations were obtained. Since the derivatives of proline were very important intermediates, so the studies are meaningful for the process of searching new drugs.