Liquid chromatographic resolution of proline and pipecolic acid derivatives on chiral stationary phases based on (+)‐(18‐crown‐6)‐2, 3, 11, 12‐tetracarboxylic acid. Issue 6 (2nd January 2018)

• Record Type: Journal Article
• Authors: Cho, Eun Sol; Sung, Ji Yeong; Jin, Jong Sung; Hyun, Myung Ho
• Is Part Of: Journal of separation science. Volume 41:Issue 6(2018)
• Page Start: 1192
• Page End: 1198
• Publication Date: 2018-01-02
• Subjects: chiral stationary phases -- enantiomer separation -- liquid chromatography -- pipecolic acid -- proline; Separation (Technology) -- Periodicals; Chromatographic analysis -- Periodicals; 543.089
• DOI: 10.1002/jssc.201700996
• Languages: English
• ISSNs: 1615-9306

Abstract

Abstract: Two liquid chromatographic chiral stationary phases based on (+)‐(18‐crown‐6)‐2, 3, 11, 12‐tetracarboxylic acid were applied to the resolution of the amide derivatives of cyclic α‐amino acids including proline and pipecolic acid. Among the five amide derivatives of proline, aniline amide was resolved best on the first chiral stationary phase, which contains two N–H tethering amide groups, with the separation factor of 1.31 and the resolution of 2.60, and on the second chiral stationary phase, which contains two N–CH3 tethering amide groups, with the separation factor of 1.57 and the resolution of 5.50. Among the five amide derivatives of pipecolic acid, 2‐naphthyl amide was resolved best on the first chiral stationary phase with the separation factor of 1.30 and the resolution of 1.75, but 1‐naphthylmethyl amide was resolved best on the second chiral stationary phase with the separation factor of 1.30 and the resolution of 2.26. In general, the second chiral stationary phase was found to be better than the first chiral stationary phase in the resolution of the amide derivatives of cyclic α‐amino acids. In this study, the second chiral stationary phase was first demonstrated to be useful for the resolution of secondary amino compounds.