An 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]

On-line racemization by high-performance liquid chromatography

CANNAZZA, Giuseppe;CARROZZO, Marina Maria;BATTISTI, UMBERTO MARIA;BRAGHIROLI, Daniela;PARENTI, Carlo
2009

Abstract

An 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.
1216
5655
5659
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]
Cannazza, Giuseppe; Carrozzo, Marina Maria; Battisti, UMBERTO MARIA; Braghiroli, Daniela; Parenti, Carlo
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/721246
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