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 |
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Keywords
- 5-Oxo-1-phenyl-pyrazolidine-3-carboxylic acid
- L-amino acid
- Optical resolution
- Organocatalyst
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Optical resolution of 5-oxo-1-phenyl-pyrazolidine-3-carboxylic acid as a new organocatalyst for organic reactions. / Tzeng, Zheng Hao; Yang, Shuen Wen; Liu, Pang Min; Chen, Kwun Min.
In: Journal of the Chinese Chemical Society, Vol. 55, No. 3, 01.01.2008, p. 626-631.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Optical resolution of 5-oxo-1-phenyl-pyrazolidine-3-carboxylic acid as a new organocatalyst for organic reactions
AU - Tzeng, Zheng Hao
AU - Yang, Shuen Wen
AU - Liu, Pang Min
AU - Chen, Kwun Min
PY - 2008/1/1
Y1 - 2008/1/1
N2 - 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.
AB - 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.
KW - 5-Oxo-1-phenyl-pyrazolidine-3-carboxylic acid
KW - L-amino acid
KW - Optical resolution
KW - Organocatalyst
UR - http://www.scopus.com/inward/record.url?scp=48349091161&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=48349091161&partnerID=8YFLogxK
U2 - 10.1002/jccs.200800091
DO - 10.1002/jccs.200800091
M3 - Article
AN - SCOPUS:48349091161
VL - 55
SP - 626
EP - 631
JO - Journal of the Chinese Chemical Society
JF - Journal of the Chinese Chemical Society
SN - 0009-4536
IS - 3
ER -