Continuous flow synthesis of the lamivudine precursor L-Menthyl Glyoxylate

Azevedo, Lais S. D.; Aguillón, Anderson R.; Lima, Marcelo T.; Leão, Raquel A. C.; Souza, Rodrigo O. M. A. de

doi:10.1007/s41981-021-00189-8

Cited by 2 publications

(1 citation statement)

References 36 publications

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“…Most of the literature covering 2020-2022 deal with the preparation of key building blocks (Al-Shameri et al, 2020;Böhmer et al, 2020;Hegarty and Paradisi, 2020;Roura Padrosa et al, 2020;Oeggl et al, 2021;Semproli et al, 2020;Teepakorn et al, 2021;Azevedo et al, 2022;Peng et al, 2022) for fine chemicals/APIs (2020)(2021)(2022). Frontiers in Catalysis frontiersin.org rather than with the total synthesis of drugs (Rinaldi et al, 2020;Wu et al, 2020;Kazan et al, 2021;Romero-Fernandez and Paradisi, 2021;Benítez-Mateos et al, 2022a;Benítez-Mateos and Paradisi, 2022).…”

Section: Active Pharmaceutical Ingredientsmentioning

confidence: 99%

What’s new in flow biocatalysis? A snapshot of 2020–2022

et al. 2023

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Flow biocatalysis is a key enabling technology that is increasingly being applied to a wide array of reactions with the aim of achieving process intensification, better control of biotransformations, and minimization of waste stream. In this mini-review, selected applications of flow biocatalysis to the preparation of food ingredients, APIs and fat- and oil-derived commodity chemicals, covering the period 2020-2022, are described.

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Section: Active Pharmaceutical Ingredientsmentioning

confidence: 99%

What’s new in flow biocatalysis? A snapshot of 2020–2022

et al. 2023

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Continuous Flow Synthesis of the Nerve Agent Antidote Pralidoxime (2‐PAM) Iodide

Gomez,

da Rocha,

Chaves

et al. 2024

ChemistrySelect

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Pralidoxime salts are important medical countermeasures towards different organophosphorus compounds, either nerve agents or pesticides, as they act as acetylcholinesterase reactivators, avoiding health issues and even death that can result from intoxication with such chemicals. In this work, we present an expeditious study focuses on the optimization of a two‐step continuous‐flow synthesis of 2‐PAM. Initial attempts to replace the solvent composition in the oxime formation reaction with acetonitrile resulted in lower yields, highlighting the significance of a polar protic solvent. Subsequent optimization under continuous‐flow conditions revealed the successful execution of oxime formation at room temperature with a residence time of 20 minutes, achieving an impressive 96 % conversion, surpassing literature‐reported conditions. The methylation step required a high residence time of 60 minutes at 120 °C for a substantial conversion of 78 %. The two‐step continuous‐flow process demonstrated robustness, yielding 75 %, with space‐time yields of 0.32 g/h and 0.18 g/h. Further concentration adjustments increased space‐time yields to 3.2 g/h and 2.2 g/h. Despite solvent incompatibility, a strategic alteration of the reaction sequence allowed for a successful cascade process, integrating the methylation step in acetonitrile and the oxime formation in water. The continuous‐flow system, incorporating a heat exchanger, exhibited stability, maintaining full conversion and a space‐time yield of 0.3 g/h over extended periods. This systematic optimization not only enhances the efficiency of 2‐PAM synthesis but also provides insights into a scalable and practical continuous‐flow cascade process.

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Continuous flow synthesis of the lamivudine precursor L-Menthyl Glyoxylate

Cited by 2 publications

References 36 publications

What’s new in flow biocatalysis? A snapshot of 2020–2022

What’s new in flow biocatalysis? A snapshot of 2020–2022

Continuous Flow Synthesis of the Nerve Agent Antidote Pralidoxime (2‐PAM) Iodide

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