Synthesis of the Antibiotic Precursor Thiazolyl‐7‐Aminocephalosporanic Acid in a Microstructured Flow System

Vanessa, Wirth,; Volkmar, Julia; Bayer, Thomas

doi:10.1002/ceat.201900077

Cited by 4 publications

(2 citation statements)

References 27 publications

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“…Wirth et al have published an interesting manuscript for the continuous synthesis of thiazolyl-7-aminocephalosporanic acid (7-TACA, 7 ) [ 89 ]; the key cefodizime intermediate. This involves a 3′-modification using methylmercaptothiazolyl acid (MMTA) on 7-ACA, the antibiotic’s backbone, as depicted in Scheme 8 .…”

Section: Antibiotic Synthesis In Flow Modementioning

confidence: 99%

Towards Antibiotic Synthesis in Continuous-Flow Processes

et al. 2023

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Continuous-flow chemistry has become a mainstream process and a notable trend among emerging technologies for drug synthesis. It is routinely used in academic and industrial laboratories to generate a wide variety of molecules and building blocks. The advantages it provides, in terms of safety, speed, cost efficiency and small-equipment footprint compared to analog batch processes, have been known for some time. What has become even more important in recent years is its compliance with the quality objectives that are required by drug-development protocols that integrate inline analysis and purification tools. There can be no doubt that worldwide government agencies have strongly encouraged the study and implementation of this innovative, sustainable and environmentally friendly technology. In this brief review, we list and evaluate the development and applications of continuous-flow processes for antibiotic synthesis. This work spans the period of 2012–2022 and highlights the main cases in which either active ingredients or their intermediates were produced under continuous flow. We hope that this manuscript will provide an overview of the field and a starting point for a deeper understanding of the impact of flow chemistry on the broad panorama of antibiotic synthesis.

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Section: Antibiotic Synthesis In Flow Modementioning

confidence: 99%

Towards Antibiotic Synthesis in Continuous-Flow Processes

et al. 2023

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“…2-Mercapto-4-methyl-5-thiazoleacetic acid (MMTAA) is a biocompatible molecule that can be used as an intermediate for the antibiotic cefodizime . The heterocyclic ring in MMTAA possesses carboxylate, mercapto, and thiazolyl groups, all of which are able to coordinate with Bi. − This provides a good platform to study the coordination behavior of Bi and the effect of the functional group on the activity.…”

Section: Introductionmentioning

confidence: 99%

A Bismuth-Based Metal–Organic Framework for Visible-Light-Driven Photocatalytic Decolorization of Dyes and Oxidation of Phenylboronic Acids

et al. 2022

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In this work, a Bi-based metal−organic framework (MOF; Bi-MMTAA) with 2-mercapto-4-methyl-5-thiazoleacetic acid (MMTAA) as the organic ligand is synthesized. The crystal structure of Bi-MMTAA was determined by single-crystal X-ray diffraction. Theoretical calculations reveal that Bi-MMTAA is a p-type semiconductor, and electrons can delocalize through the πconjugation when excited by a photon with an energy higher than the Bi-MMTAA band gap, which is beneficial to charge separation and transfer. The photoelectrical properties suggest that free electrons can be produced over Bi-MMTAA under light irradiation. The photocatalytic results suggest that Bi-MMTAA can decolorize rhodamine B (RhB) and oxidize phenylboronic acid to phenol under visible light (λ > 420 nm), with superoxide radicals being the main reactive oxygen species. Our results enrich the family of Bi-based MOFs and may inspire further exploration of Bi-based MOFs, including both synthesis and potential applications.

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Four-membered ring systems

Anaya

Sánchez

2021

Progress in Heterocyclic Chemistry

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Synthesis of the Antibiotic Precursor Thiazolyl‐7‐Aminocephalosporanic Acid in a Microstructured Flow System

Cited by 4 publications

References 27 publications

Towards Antibiotic Synthesis in Continuous-Flow Processes

Towards Antibiotic Synthesis in Continuous-Flow Processes

A Bismuth-Based Metal–Organic Framework for Visible-Light-Driven Photocatalytic Decolorization of Dyes and Oxidation of Phenylboronic Acids

Four-membered ring systems

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