Green Chemistry Articles of Interest to the Pharmaceutical Industry

Braun, Marie-Gabrielle; Engl, Oliver D.; Fraunhoffer, Kenneth J.; Hayler, John; Hickey, Matthew; Latham, Jonathan; Lovelle, Lucie E.; McLaws, Mark D.; Richardson, Paul; Roosen, Philipp C.; Steven, Alan; Terrett, Jack A.; White, Timothy; Yin, Jingjun

doi:10.1021/acs.oprd.0c00154

Cited by 6 publications

(4 citation statements)

References 2 publications

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“…In addition to this intriguing feature, the reaction also benefits from the low-waste generation, with most of the examined substrates not necessitating additional reagents and generating NaCl as the only waste. Although this process might be of lower value for the synthesis of simple primary or secondary amides, the aforementioned advantages somehow show high atom-economic and sustainable chemistry credentials, and would thus serve as a stand-out amidation strategy especially for the cases where N -alkoxycarbonyl motif is inevitably needed. We viewed this as an opportunity for further improvements that could lead to possible applications in larger scale processes.…”

Section: Introductionmentioning

confidence: 99%

N-Chloro-N-sodio-carbamates as a Practical Amidating Reagent for Scalable and Sustainable Amidation of Aldehydes under Visible Light

Jeon

Lee

Chang

2021

Org. Process Res. Dev.

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Herein, we describe the scalability and sustainability investigations toward the visible light-mediated amidation of aldehydes with N-chloro-N-sodio-carbamates. The practicality credentials of N-chloro-N-sodio-carbamates for their use in multigram scale amidation reactions are proven by scale-up productions and thermogravimetric analysis. The described amidation, which was previously hampered in sustainability perspectives by the use of α,α,α-trifluorotoluene solvent, is now improved through re-optimizations using ethyl acetate as an alternative green solvent. The generality of multigram scale amidations is demonstrated by the conversion of a selected list of aldehydes, in which the corresponding amides can be isolated in high purity without the need for special purification procedures.

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Section: Introductionmentioning

confidence: 99%

N-Chloro-N-sodio-carbamates as a Practical Amidating Reagent for Scalable and Sustainable Amidation of Aldehydes under Visible Light

Jeon

Lee

Chang

2021

Org. Process Res. Dev.

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“…Hence, biocatalysis is now added among other well‐established tools in green chemistry, such as organocatalysis, multicomponent reactions, and solvent‐free synthesis, just to cite a few examples. A broader view on the use of such approaches in the synthesis of pharmaceuticals is beyond the scope of this work and can be found in other excellent reviews on the topic 62–64 . Herein, we focus on examples, selected from recent literature, that show the successful use of biocatalysis in the synthesis of chiral APIs.…”

Section: Biocatalytic Approaches For Chiral Drugs Preparation In Phar...mentioning

confidence: 99%

“…A broader view on the use of such approaches in the synthesis of pharmaceuticals is beyond the scope of this work and can be found in other excellent reviews on the topic. [62][63][64] Herein, we focus on examples, selected from recent literature, that show the successful use of biocatalysis in the synthesis of chiral APIs.…”

Section: Biocatalytic Approaches For Chiral Drugs Preparation In Phar...mentioning

confidence: 99%

Biocatalysis: A smart and green tool for the preparation of chiral drugs

et al. 2022

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Over the last decades, biocatalysis has achieved growing interest thanks to its potential to enable high efficiency, high yield, and eco-friendly processes aimed at the production of pharmacologically relevant compounds. Particularly, biocatalysis proved an effective and potent tool in the preparation of chiral molecules, and the recent innovations of biotechnologies and nanotechnologies open up a new era of further developments in this field. Different strategies are now available for the synthesis of chiral drugs and their intermediates. Enzymes are green tools that offer several advantages, associated both to catalysis and environmentally friendly reactants. Specifically, the use of enzymes isolated from biological sources or of whole-cell represents a valuable approach to obtain pharmaceutical products. The sustainability, the higher efficiency, and cost-effectiveness of biocatalytic reactions result in improved performance and properties that can be translated from academia to industry. In this review, we focus on biocatalytic approaches for synthesizing chiral drugs or their intermediates. Aiming to unveil the potentialities of biocatalysis systems, we discuss different examples of innovative biocatalytic approaches and their applications in the pharmaceutical industry.

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“…The reaction was incomplete even with an excess amount of Na 2 S 2 O 8 , presumably caused by the decomposition of Na 2 S 2 O 8 in DMF. After optimization, the researchers were able to identify safer and greener alternative conditions to effect this oxidation reaction, namely, the use of potassium ferricyanide (K 3 FeCN 6 ) in the presence of aqueous KOH at 70–90 °C, which afforded a cleaner reaction profile and a higher isolated yield …”

Section: Potential Safety Hazards With Dmfmentioning

confidence: 99%

Potential Safety Hazards Associated with Using N,N-Dimethylformamide in Chemical Reactions

Yang

Sheng

Huang

2020

Org. Process Res. Dev.

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N,N-Dimethylformamide (DMF) is frequently used as a solvent because of its unique physical properties that allow it to solubilize both organic and inorganic substances. It has also found broad applications as a catalyst for a variety of chemical transformations and as a donor for many functional groups in synthetic organic chemistry. However, DMF is incompatible with a wide variety of substances and has resulted in many incidents over the years. Analysis of literature information indicates that those incompatible substances can be categorized as acids, bases, halogenated reagents, oxidants, and reductants. This comprehensive review of the potential hazards of using DMF in chemical reactions will serve as an educational resource to promote awareness of such safety hazards in the broader chemistry community and encourage scientists to develop appropriate control strategies to mitigate the potential safety risks associated with the use of DMF in chemical reactions.

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Green Chemistry Articles of Interest to the Pharmaceutical Industry

Cited by 6 publications

References 2 publications

N-Chloro-N-sodio-carbamates as a Practical Amidating Reagent for Scalable and Sustainable Amidation of Aldehydes under Visible Light

N-Chloro-N-sodio-carbamates as a Practical Amidating Reagent for Scalable and Sustainable Amidation of Aldehydes under Visible Light

Biocatalysis: A smart and green tool for the preparation of chiral drugs

Potential Safety Hazards Associated with Using N,N-Dimethylformamide in Chemical Reactions

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