A Convenient Method for the Enantiomeric Separation of alpha-Amino Acid Esters as Benzophenone Imine Schiff Base Derivatives

作者：Huang Hu; Xu Wen Jun; Jin Jing Yu; Hong Joon Hee; Shin Hyun Jae; Lee Wonjae^*

来源：Archives of Pharmacal Research, 2012, 35(6): 1015-1019.

DOI：10.1007/s12272-012-0609-6

• Chiral stationary phase
• Benzophenone imine derivative
• Enantiomer separation

A convenient liquid chromatographic method for the separation of alpha-amino acid esters as benzophenone Schiff base derivatives on coated chiral stationary phases (CSPs) (Chiralcel OD-H, Chiralcel OD, Chiralpak AD-H, Chiralpak AD, and Chiralpak AS) or covalently immobilized CSPs (Chiralpak IA, Chiralpak IB, and Chiralpak IC) derived from polysaccharide derivatives is described. Benzophenone imine derivatives of alpha-amino acid esters were readily prepared by stirring benzophenone imine and the hydrochloride salts of alpha-amino acid esters in 2-propanol. The chromatographic separations were conducted at a flow rate 1.0 mL/min and a detection wavelength of 254 nm; 0.5% 2-propanol/hexane (v/v) was used on CSPs. In general, the resolution of Chiralpak IC was superior to those of the other CSPs. In addition, the resolutions of other arylimine derivatives of alpha-amino acid esters and the effects of different mobile phases on the enantiomeric separation of alpha-amino acid esters as benzophenone imine derivatives on Chiralpak IC were investigated.

• 出版日期2012-6