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HPLC Resolution (hplc + resolution)
Selected AbstractsEnantioselective HPLC resolution of synthetic intermediates of armodafinil and related substancesJOURNAL OF SEPARATION SCIENCE, JSS, Issue 6-7 2008Ramisetti Nageswara Rao Abstract Armodafinil is a unique psychostimulant recently approved by the US Food and Drug Administration for the treatment of narcolepsy. The chromatographic resolution of its chiral intermediates including related substances in the total synthesis of armodafinil was studied on polysaccharide-based stationary phases, viz. cellulose tris-(3,5-dimethylphenylcarbamate) (Chiralcel OD-H) and amylose tris-(3,5-dimethylphenylcarbamate) (Chiralpak AD-H) by HPLC. The effects of 1-propanol, 2-propanol, ethanol, and trifluoroacetic acid added to the mobile phase and of column temperature on resolution were studied. A good separation was achieved on cellulose-based Chiralcel OD-H column compared to amylose-based Chiralpak AD-H. The effects of structural features of the solutes and solvents on discrimination between the enantiomers were examined. Baseline separation with Rs >1.38 was obtained using a mobile phase containing n -hexane,ethanol,TFA (75:25:0.15 v/v/v). Detection was carried out at 225 nm with photodiode array detector while identification of enantiomers was accomplished by a polarimetric detector connected in series. The method was found to be suitable not only for process development of armodafinil but also for determination of the enantiomeric purity of bulk drugs and pharmaceuticals. [source] Evaluation of HPLC columns: A study on surface homogeneity of chemically bonded stationary phasesJOURNAL OF SEPARATION SCIENCE, JSS, Issue 3-4 2003Bogus, aw Buszewski Abstract The aim of the current work is to study the heterogeneity of the adsorbent surface on the basis of physicochemical investigations and chromatographic tests. A series of packing materials with octadecyl chains chemically bonded to a silica matrix were prepared for this purpose. The surface and structural properties of bare silica and silica-based octadecyl phases were characterized by porosimetry, elemental analysis, 29Si CP/MAS NMR, etc. The most advanced characterization methods based on adsorption microcalorimetry (heat of wetting) measurements were employed to obtain information about the heterogeneity and topography of unmodified and modified silica gel. For the chromatographic study, these phases were evaluated on the basis of the retention data under non-aqueous conditions. A test series of solutes with various chemical properties, such as pK a values, was used. It was found that heterogeneity of the packing surface results in low HPLC resolution. Use of a non-aqueous mobile phase (n -hexane) reduces analytical interference by eliminating hydrophobic interactions between alkyl ligands and the analyte. [source] Effective HPLC resolution of [4]heterohelicenium dyes on chiral stationary phases using reversed-phase eluentsCHIRALITY, Issue 8 2007Claudio Villani Abstract [4]Heterohelicenium cations 1a,c adopt a twisted helical structure that renders them chiral. They are configurationally stable and their enantiomers have been resolved, for the first time, by HPLC on Chiralcel OD-RH and Chirobiotic TAG chiral stationary phases (CSPs). Chiral cations 1a,c have been resolved by HPLC using water-based eluents containing KPF6 as additive. The elution order of the analyte enantiomers was determined by on-line CD detection, and was found to be opposite on the two CSPs. The effect of mobile phase composition and analyte structure on retention and enantioselectivity was investigated. Chirality 19:601,606, 2006 © 2006 Wiley-Liss, Inc. [source] Synthesis and HPLC enantioseparation of the cyclopropane analogue of valine (c3Val)CHIRALITY, Issue 1 2005Ana I. Jiménez Abstract A new and efficient method is presented for the preparation of the N -Boc-protected cyclopropane analogue of valine, 1-(N-tert -butoxycarbonyl)amino-2,2-dimethylcyclopropanecarboxylic acid, both in racemic and enantiomerically pure forms. Cyclopropanation of the exocyclic double bond of 2-phenyl-4-isopropylidene-5(4H)-oxazolone with diazomethane followed by elaboration of the heterocyclic moiety provided multigram quantities of the racemic target compound. Subsequent HPLC resolution of a racemic precursor on a noncommercial chiral stationary phase has given access to enantiomerically pure products. Almost 1.5 g of the first-eluted enantiomer and 1.0 g of the second-eluted enantiomer have been isolated in optically pure form using a 150 × 20 mm ID column containing mixed 10-undecenoate/3,5-dimethylphenylcarbamate of cellulose covalently bonded to allylsilica gel with a mixture of hexanes/tert -butyl methyl ether/ethyl acetate as the mobile phase. Chirality 17:22,29, 2005. ©2004 Wiley-Liss, Inc. [source] Determination of the absolute configuration of bicyclo[3.3.1]nonane-2,7-dione by circular dichroism spectroscopy and chemical correlationCHIRALITY, Issue 10 2001Eugenius Butkus Abstract A study of the enantiomers of bicyclo[3.3.1]nonane-2,7-dione, a chiral molecule containing two carbonyl chromophores, was performed. Enantiomers of this structure were obtained by HPLC resolution and the (+)-(1R,5S)-enantiomer by enantiospecific synthesis from(+)-(1S,5S)-bicyclo[3.3.1]nonane-2,6-dione. The title structure is an interesting molecule to demonstrate the validity of the octant rule. The location of the major chair,chair conformer into octants placing each chromophore into the origin of the octants led to the opposite configuration assignments. In order to prove unequivocally absolute configuration, enantiospecific synthesis of the title compound was carried out. The kinetic resolution of racemic bicyclo[3.3.1]nonane-2,6-dione using baker's yeast afforded (+)-(1S,5S)-2,6-dione. Employing a reaction sequence analogous to one developed earlier by us with racemic substrates led to carbonyl group shift giving enantiomerically pure (+)-(1R,5S)-bicyclo[3.3.1]nonane-2,7-dione. The absolute configuration of the investigated compound was established by combined use of the octant rule and chemical correlation. Chirality 13:694,698, 2001. © 2001 Wiley-Liss, Inc. [source] | ||||||||||