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...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Hindawi Limited
2013-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2013/386238 |
| Summary: | 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. |
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| ISSN: | 2090-9063 2090-9071 |