Enantiomer Separation by HPLC with Urea Derivatives of (R)-Phenylglycine as Novel Chiral Stationary Phases

Abstract

Two novel chiral stationary phases derived from (R)- and (S)-1-(1-naphthyl) ethylamine with (R)-phenylglycine chemically bonded to (3-aminopropyl)silanized silica, [5] and [6], which contain two asymmetric carbon atoms attached to two nitrogen atoms of the ureylene group, have been prepared. These phases showed good enantioselectivity for derivatives of amino acid, amine, carboxylic acid and alcohol enantiomers. Especially excellent separation factors were obtained in enantiomeric separation of aromatic amine and carboxylic acid in the form of 3, 5-dinitrobenzoyl and 3, 5-dinitroanilide derivatives respectively upon phase [6]. It is noticed some enantiomers were resolved directly without any prederivatization on these phases. For example, enantiomers of both E- and Z-isomers of S-3308 (1-(2, 4- di chloropheny1)-4, 4-dimethy1-2-(l, 2, 4-triazol-1-y1)-1-penten-3-ol) are well resolved simul taneously with [5].