Resolution of (±)‐β‐methylphenylethylamine by a novel chiral stationary phase for Pirkle‐type column chromatography

Abstract

In this study, a new Pirkle-type chiral column stationary phase for resolution of beta-methylphenylethyl amine was described by using activated Sepharose 4B as a matrix, L-tyrosine as a spacer arm, and an aromatic amine derivative of L-glutamic acid as a ligand. The binding capacities of the stationary phase were determined at different pH values (pH = 6, 7, and 8) using buffer solutions as mobile phase, and enantiomeric excess (ee) was determined by HPLC equipped with chiral column. The ee was found to be 47%.

Design, preparation and application of a Pirkle-type chiral stationary phase for enantioseparation of some racemic organic acids and molecular dynamics studies

“…: [33][34][35] Preparation of N-p-nitrobenzyl-(R)-2-amino-1-butanol (3): 4.46 g (50 mmol) (R)-2-amino-1-butanol (2), 1.3 g (12.3 mmol) Na 2 CO 3 and 2.7 g (12.5 mmol) p-nitrobenzyl bromide (1) in 100 mL benzene were placed in a 250 mL two-necked round bottomed flask equipped with an Dean-Stark apparatus, which applies to separate water from refluxing benzene. The mixture was refluxed by stirring at 110 º C for 12 h in an oil bath under dry N 2 .…”

The Preparation of a New Protein Based HPLC Column Packing Material and Enantiomeric Resolution of Some Pharmaceutical Related Compounds via This Column

“…Bununla birlikte 1976'da Mikas ve çalışma grubu silikajele küçük bir kiral molekül tutturarak yeni bir CSP türüne zemin oluşturdular. Pirkle ve çalışma arkadaşları bu tip kiral sabit fazları geliştirerek, bu kolon dolgu materyallerinin Pirkle tip kiral sabit fazlar adı altında literatüre girmesini sağladılar [9,10,30,51]. Bu tip CSP'ler de, ya π-elektron alıcı grup ya π-elektron verici grup ya da her iki grubu birden içeren kiral bir molekül, iyonik veya kovalent bağlarla silika jele bağlanır.…”

Chiral Separations: Fundamental Review 2010

“…The performance of Pirkle-type CSPs and polysaccharide-based CSPs for the resolution of the enantiomers of six phthalans was evaluated (131). A new Pirkletype CSP was obtained using activated Sepharose 4B as a matrix, L-tyrosine as a spacer arm, and an aromatic amine derivative of L-glutamic acid as a ligand, and this CSP was used in the enantiomeric resolution of (±)-β-methylphenylethylamine (132). A brush-type CSP was prepared in-column using click chemistry and a silica monolith to synthesize a proline-derived CSP and was used to enantioseparate four model analytes (133).…”