EnglishAn on-column stopped-flow bidimensional recycling HPLC procedure was developed to obtain an enantiomeric enrichment starting from a racemic mixture. The method developed was applied to two chiral compounds of pharmaceutical interest, (±)(R,S)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide (1) and (±)-7-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide ((±)IDRA21, (2)), since the pharmacological activity of the two benzothiadiazine derivatives investigated has been ascribed to only one enantiomer. Starting from a racemic mixture it was possible to obtain about 95% of pure enantiomer. The procedure was applied both in reverse-phase mode and in normal-phase mode. The scaled up and automatization of the novel analytical HPLC procedure represents a powerful tool to obtain pure enantiomer starting from racemic compounds without cumbersome stereoselective synthesis or expensive enantiopurification processes.
On-line racemization by high-performance liquid chromatography / Cannazza, Giuseppe; Carrozzo, Marina Maria; Battisti, UMBERTO MARIA; Braghiroli, Daniela; Parenti, Carlo. - In: JOURNAL OF CHROMATOGRAPHY A. - ISSN 0021-9673. - STAMPA. - 1216(2009), pp. 5655-5659. [10.1016/j.chroma.2009.05.057]
| Data di pubblicazione: | 2009 | |
| Titolo: | On-line racemization by high-performance liquid chromatography | |
| Autore/i: | Cannazza, Giuseppe; Carrozzo, Marina Maria; Battisti, UMBERTO MARIA; Braghiroli, Daniela; Parenti, Carlo | |
| Autore/i UNIMORE: | ||
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/j.chroma.2009.05.057 | |
| Rivista: | ||
| Volume: | 1216 | |
| Pagina iniziale: | 5655 | |
| Pagina finale: | 5659 | |
| Codice identificativo ISI: | WOS:000268074800006 | |
| Codice identificativo Scopus: | 2-s2.0-67649382946 | |
| Codice identificativo Pubmed: | 19539938 | |
| Citazione: | On-line racemization by high-performance liquid chromatography / Cannazza, Giuseppe; Carrozzo, Marina Maria; Battisti, UMBERTO MARIA; Braghiroli, Daniela; Parenti, Carlo. - In: JOURNAL OF CHROMATOGRAPHY A. - ISSN 0021-9673. - STAMPA. - 1216(2009), pp. 5655-5659. [10.1016/j.chroma.2009.05.057] | |
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