Optical resolution of 5-oxo-1-phenyl-pyrazolidine-3-carboxylic acid as a new organocatalyst for organic reactions

Zheng Hao Tzeng; Shuen Wen Yang; Pang Min Liu; Kwun Min Chen

doi:10.1002/jccs.200800091

Optical resolution of 5-oxo-1-phenyl-pyrazolidine-3-carboxylic acid as a new organocatalyst for organic reactions

Zheng Hao Tzeng, Shuen Wen Yang, Pang Min Liu, Kwun Min Chen

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

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	https://doi.org/10.1002/jccs.200800091
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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10.1002/jccs.200800091

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title = "Optical resolution of 5-oxo-1-phenyl-pyrazolidine-3-carboxylic acid as a new organocatalyst for organic reactions",

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.",

keywords = "5-Oxo-1-phenyl-pyrazolidine-3-carboxylic acid, L-amino acid, Optical resolution, Organocatalyst",

author = "Tzeng, {Zheng Hao} and Yang, {Shuen Wen} and Liu, {Pang Min} and Chen, {Kwun Min}",

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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

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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.

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