Abstract
Optical resolution of racemic 5-oxo-1-phenyl-pyrazolidine-3-carboxylic acid 2 with L-amino acid methyl ester via the diastereomers formation was investigated. Treatment of racemic 5-oxo-1-phenylpyrazolidine-3-carboxylic acid 2 with L-valine methyl ester gave diastereomers with a total yield of 86%. The diastereomeric dipeptides can be easily separated by flash column chromatography. Acidic cleavage of the derived diastereomers gave both the optically pure (+)-(R)- and (-)-(S)-5-oxo-1-phenyl-pyrazolidine-3-carboxylic acid ((+)-(R)-2 and (-)-(S)-2) with a total yield of 94% and 95%, respectively.
| Original language | English |
|---|---|
| Pages (from-to) | 626-631 |
| Number of pages | 6 |
| Journal | Journal of the Chinese Chemical Society |
| Volume | 55 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - 2008 Jan 1 |
Keywords
- 5-Oxo-1-phenyl-pyrazolidine-3-carboxylic acid
- L-amino acid
- Optical resolution
- Organocatalyst
ASJC Scopus subject areas
- Chemistry(all)
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Cite this
Tzeng, Z. H., Yang, S. W., Liu, P. M., & Chen, K. M. (2008). Optical resolution of 5-oxo-1-phenyl-pyrazolidine-3-carboxylic acid as a new organocatalyst for organic reactions. Journal of the Chinese Chemical Society, 55(3), 626-631. https://doi.org/10.1002/jccs.200800091