Comparison of a Batch and Flow Approach for the Lipase-Catalyzed Resolution of a Cyclopropanecarboxylate Ester, A Key Building Block for the Synthesis of Ticagrelor

Katharina G. Hugentobler; Marcello Rasparini; Lisa A. Thompson; Katherine E. Jolley; A. John Blacker; Nicholas J. Turner

doi:10.1021/acs.oprd.6b00346

Comparison of a Batch and Flow Approach for the Lipase-Catalyzed Resolution of a Cyclopropanecarboxylate Ester, A Key Building Block for the Synthesis of Ticagrelor

Katharina G. Hugentobler, Marcello Rasparini, Lisa A. Thompson, Katherine E. Jolley, A. John Blacker, Nicholas J. Turner^*

^*Corresponding author for this work

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

Abstract

In this study a batch reactor process is compared to a flow chemistry approach for lipase-catalyzed resolution of the cyclopropanecarboxylate ester (±)-3. (1R,2R)-3 is a precursor of the amine (1R,2S)-2 which is a key building block of the API ticagrelor. For both flow and batch operation, the biocatalyst could be recycled several times, whereas in the case of the flow process the reaction time was significantly reduced.

Original language	English
Pages (from-to)	195-199
Number of pages	5
Journal	Organic Process Research and Development
Volume	21
Issue number	2
Early online date	22 Dec 2016
DOIs	https://doi.org/10.1021/acs.oprd.6b00346
Publication status	Published - 17 Feb 2017

Keywords

batch reactor
enzyme catalysis
flow chemistry
Thermomyces lanuginosus lipase
ticagrelor

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10.1021/acs.oprd.6b00346

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Hugentobler, K. G., Rasparini, M., Thompson, L. A., Jolley, K. E., Blacker, A. J., & Turner, N. J. (2017). Comparison of a Batch and Flow Approach for the Lipase-Catalyzed Resolution of a Cyclopropanecarboxylate Ester, A Key Building Block for the Synthesis of Ticagrelor. Organic Process Research and Development, 21(2), 195-199. https://doi.org/10.1021/acs.oprd.6b00346

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abstract = "In this study a batch reactor process is compared to a flow chemistry approach for lipase-catalyzed resolution of the cyclopropanecarboxylate ester (±)-3. (1R,2R)-3 is a precursor of the amine (1R,2S)-2 which is a key building block of the API ticagrelor. For both flow and batch operation, the biocatalyst could be recycled several times, whereas in the case of the flow process the reaction time was significantly reduced.",

keywords = "batch reactor, enzyme catalysis, flow chemistry, Thermomyces lanuginosus lipase, ticagrelor",

author = "Hugentobler, {Katharina G.} and Marcello Rasparini and Thompson, {Lisa A.} and Jolley, {Katherine E.} and Blacker, {A. John} and Turner, {Nicholas J.}",

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doi = "10.1021/acs.oprd.6b00346",

language = "English",

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Comparison of a Batch and Flow Approach for the Lipase-Catalyzed Resolution of a Cyclopropanecarboxylate Ester, A Key Building Block for the Synthesis of Ticagrelor. / Hugentobler, Katharina G.; Rasparini, Marcello; Thompson, Lisa A. et al.
In: Organic Process Research and Development, Vol. 21, No. 2, 17.02.2017, p. 195-199.

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

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T1 - Comparison of a Batch and Flow Approach for the Lipase-Catalyzed Resolution of a Cyclopropanecarboxylate Ester, A Key Building Block for the Synthesis of Ticagrelor

AU - Hugentobler, Katharina G.

AU - Rasparini, Marcello

AU - Thompson, Lisa A.

AU - Jolley, Katherine E.

AU - Blacker, A. John

AU - Turner, Nicholas J.

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AB - In this study a batch reactor process is compared to a flow chemistry approach for lipase-catalyzed resolution of the cyclopropanecarboxylate ester (±)-3. (1R,2R)-3 is a precursor of the amine (1R,2S)-2 which is a key building block of the API ticagrelor. For both flow and batch operation, the biocatalyst could be recycled several times, whereas in the case of the flow process the reaction time was significantly reduced.

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KW - enzyme catalysis

KW - flow chemistry

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Comparison of a Batch and Flow Approach for the Lipase-Catalyzed Resolution of a Cyclopropanecarboxylate Ester, A Key Building Block for the Synthesis of Ticagrelor

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Keywords

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