Microwave-Assisted Synthesis of (±)-Mandelic Acid-d5, Optical Resolution, and Absolute Configuration Determination
An efficient microwave-assisted synthesis of (±)-mandelic acid-d5 was developed. The racemic mixture was resolved by diastereomeric salt formation using 1-phenylethylamine enantiomers as resolving agents. At each step, the resolution process was checked by determining mandelic acid-d5 enantiomer ee...
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| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Wiley
2013-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2013/386238 |
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| author | Claudio Bruno Giovanni Lentini Angelo Lovece Maria Maddalena Cavalluzzi Alessia Carocci Alessia Catalano Carlo Franchini |
| author_facet | Claudio Bruno Giovanni Lentini Angelo Lovece Maria Maddalena Cavalluzzi Alessia Carocci Alessia Catalano Carlo Franchini |
| author_sort | Claudio Bruno |
| collection | DOAJ |
| description | An efficient microwave-assisted synthesis of (±)-mandelic acid-d5 was developed. The racemic mixture was resolved by diastereomeric salt formation using 1-phenylethylamine enantiomers as resolving agents. At each step, the resolution process was checked by determining mandelic acid-d5 enantiomer ee values directly on fractional crystallized diastereomeric salts by chiral capillary electrophoresis analysis. Highly enriched (−)- and (+)-mandelic acid-d5 (95% and 90% ee, resp.) were obtained and their absolute configurations—R and S, respectively—were determined by correlation of the (−)-mandelic acid-d5 circular dichroism spectrum to the (R)-mandelic acid one. |
| format | Article |
| id | doaj-art-9e5cafb1ecb040b59ee7b20eb93dcd47 |
| institution | OA Journals |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2013-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-9e5cafb1ecb040b59ee7b20eb93dcd472025-08-20T02:18:32ZengWileyJournal of Chemistry2090-90632090-90712013-01-01201310.1155/2013/386238386238Microwave-Assisted Synthesis of (±)-Mandelic Acid-d5, Optical Resolution, and Absolute Configuration DeterminationClaudio Bruno0Giovanni Lentini1Angelo Lovece2Maria Maddalena Cavalluzzi3Alessia Carocci4Alessia Catalano5Carlo Franchini6Dipartimento Farmaco-Chimico, Facoltà di Farmacia, Università degli Studi di Bari “Aldo Moro”, via Orabona 4, 70126 Bari, ItalyDipartimento Farmaco-Chimico, Facoltà di Farmacia, Università degli Studi di Bari “Aldo Moro”, via Orabona 4, 70126 Bari, ItalyDipartimento Farmaco-Chimico, Facoltà di Farmacia, Università degli Studi di Bari “Aldo Moro”, via Orabona 4, 70126 Bari, ItalyDipartimento Farmaco-Chimico, Facoltà di Farmacia, Università degli Studi di Bari “Aldo Moro”, via Orabona 4, 70126 Bari, ItalyDipartimento Farmaco-Chimico, Facoltà di Farmacia, Università degli Studi di Bari “Aldo Moro”, via Orabona 4, 70126 Bari, ItalyDipartimento Farmaco-Chimico, Facoltà di Farmacia, Università degli Studi di Bari “Aldo Moro”, via Orabona 4, 70126 Bari, ItalyDipartimento Farmaco-Chimico, Facoltà di Farmacia, Università degli Studi di Bari “Aldo Moro”, via Orabona 4, 70126 Bari, ItalyAn efficient microwave-assisted synthesis of (±)-mandelic acid-d5 was developed. The racemic mixture was resolved by diastereomeric salt formation using 1-phenylethylamine enantiomers as resolving agents. At each step, the resolution process was checked by determining mandelic acid-d5 enantiomer ee values directly on fractional crystallized diastereomeric salts by chiral capillary electrophoresis analysis. Highly enriched (−)- and (+)-mandelic acid-d5 (95% and 90% ee, resp.) were obtained and their absolute configurations—R and S, respectively—were determined by correlation of the (−)-mandelic acid-d5 circular dichroism spectrum to the (R)-mandelic acid one.http://dx.doi.org/10.1155/2013/386238 |
| spellingShingle | Claudio Bruno Giovanni Lentini Angelo Lovece Maria Maddalena Cavalluzzi Alessia Carocci Alessia Catalano Carlo Franchini Microwave-Assisted Synthesis of (±)-Mandelic Acid-d5, Optical Resolution, and Absolute Configuration Determination Journal of Chemistry |
| title | Microwave-Assisted Synthesis of (±)-Mandelic Acid-d5, Optical Resolution, and Absolute Configuration Determination |
| title_full | Microwave-Assisted Synthesis of (±)-Mandelic Acid-d5, Optical Resolution, and Absolute Configuration Determination |
| title_fullStr | Microwave-Assisted Synthesis of (±)-Mandelic Acid-d5, Optical Resolution, and Absolute Configuration Determination |
| title_full_unstemmed | Microwave-Assisted Synthesis of (±)-Mandelic Acid-d5, Optical Resolution, and Absolute Configuration Determination |
| title_short | Microwave-Assisted Synthesis of (±)-Mandelic Acid-d5, Optical Resolution, and Absolute Configuration Determination |
| title_sort | microwave assisted synthesis of mandelic acid d5 optical resolution and absolute configuration determination |
| url | http://dx.doi.org/10.1155/2013/386238 |
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