2021-03-01
Combining incompatible processes for deracemization of a Praziquantel derivative under flow conditions
Publication
Publication
Angew. Chem. Int. Ed. , Volume 60 - Issue 10 p. 5279- 5282
An efficient deracemization method for conversion of the racemate to the desirable ( R )‐enantiomer has been developed by coupling incompatible racemization and crystallization processes. By a library approach a derivative that crystallizes as a conglomerate in the solid phase has been identified. Racemization occurs via reversible hydrogenation over a palladium on carbon (Pd/C) packed column at 130 °C, whereas deracemization is achieved by alternating crystal growth/dissolution steps with temperature cycling between 5‐15 °C. These incompatible processes are combined by means of a flow system. Complete deracemization of the solid phase to the desired ( R )‐enantiomer (98% ee) takes place. Such an unprecedented deracemization by a decoupled crystallization/racemization approach can readily be turned into a practical process, and opens new opportunities for the development of essential enantiomerically pure building blocks that require harsh methods for racemization.
| Additional Metadata | |
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| Wiley-VCH | |
| European Union Horizon 2020 | |
| doi.org/10.1002/anie.202013502 | |
| Angew. Chem. Int. Ed. | |
| Organisation | Self-Organizing Matter |
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Valenti, G., Tinnemans, P., Baglai, I., Noorduin, W., Kaptein, B., Leeman, M., … Kellogg, R. (2021). Combining incompatible processes for deracemization of a Praziquantel derivative under flow conditions. Angew. Chem. Int. Ed., 60(10), 5279–5282. doi:10.1002/anie.202013502 |
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