The development of an environmentally benign synthesis of sildenafil citrate (Viagra™) and its assessment by Green Chemistry metrics

Dunn, Peter J.; Galvin, Stephen; Hettenbach, Kevin

doi:10.1039/b312329d

Cited by 183 publications

(108 citation statements)

References 5 publications

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“…As a consequence process solvents are responsible for the majority of energy use, waste, and greenhouse gas emissions [40]. This makes the minimisation of solvent use and greener substitutions a priority, and is often an easy target in green chemistry initiatives [41]. Although solvent-less chemistry has always been of interest to green chemists [42,43], it is not generally applicable to the synthesis of pharmaceuticals and other fine chemicals.…”

Section: Solvent Selection For Exploratory Chemistrymentioning

confidence: 99%

Tools and techniques for solvent selection: green solvent selection guides

Byrne

Jin

Paggiola

et al. 2016

Sustain Chem Process

1,067

737

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Driven by legislation and evolving attitudes towards environmental issues, establishing green solvents for extractions, separations, formulations and reaction chemistry has become an increasingly important area of research. Several general purpose solvent selection guides have now been published with the aim to reduce use of the most hazardous solvents. This review serves the purpose of explaining the role of these guides, highlighting their similarities and differences. How they can be used most effectively to enhance the greenness of chemical processes, particularly in laboratory organic synthesis and the pharmaceutical industry, is addressed in detail.

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Section: Solvent Selection For Exploratory Chemistrymentioning

confidence: 99%

Tools and techniques for solvent selection: green solvent selection guides

Byrne

Jin

Paggiola

et al. 2016

Sustain Chem Process

1,067

737

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“…[43] The manufacture of Viagra (sildenafil) was improved to reduce solvent usage from 1700 to 7 l/kg. [44] A new route to metal oxides developed by Süd Chemie replaces dissolution in nitric acid followed by base precipitation with a mild aerobic treatment of the metal in aqueous carboxylic acid, reducing the process water by 95%. [45] Mechanochemical methods offer solvent-free (or minimal solvent) routes to industrial materials and are therefore of great interest in devising more sustainable processes.…”

Section: Introductionmentioning

confidence: 99%

Mechanochemistry: opportunities for new and cleaner synthesis

et al. 2012

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Citation for published item:tmesD F vF nd edmsD gF tF nd folmD gF nd frgD hF nd gollierD F nd pri § s § i¡ D F nd qrepioniD pF nd rrrisD uF hF wF nd ryettD qF nd tonesD F nd uresD eF nd wkD tF nd winiD vF nd yrpenD eF qF nd rkinD sF F nd herouseD F gF nd teedD tF F nd ddellD hF gF @PHIPA 9wehnohemistry X opportunities for new nd lener synthesisF9D ghemil soiety reviewsFD RI @IAF ppF RIQERRUF Further information on publisher's website: Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details.

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“…It is a useful tool for the evaluation of rapid processes and is based on generated waste [29][30][31][32]. The environmental-factor may be obtained for (a) the synthesis step (SYS); (b) for the synthesis and product isolation steps (SYS + PIS); and (c) for the synthesis and workup steps (SYS + PIS + PPS) [39] (Fig.…”

Section: Atom Economy (Ae) Reaction Mass Efficiency (Rme)mentioning

confidence: 99%

“…Such criteria describe the energy demand, toxicity and the cost of chemicals, auxiliaries and equipment used during a product or process of life cycle stages. There are some other metrics which can also be used such as atom economy (AE) [26,27], reaction mass efficiency (RME) [28], environmental factor (E-factor) [29][30][31][32], effective mass yield [33], mass intensity [34] and the process profile [35].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Synthesis of Methyl 3-Chloro-5-(4,6-dimethoxypyrimidin- 2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate Using Green Metrics

Gilbile¹,

Bhavani²,

Vyas³

2017

Asian J. Chem.

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A modified synthesis of methyl 3-chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate (halosulphuron) is described. The merits of the synthesis are (i) one pot chlorination of methyl 1-methyl-1H-pyrazole-4-carboxylate (1) in presence of sulphuryl chloride resulting in methyl 3,5-dichloro-1-methyl-1H-pyrazole-4-carboxylate (2) (ii) conversion of 3-chloro-5-mercapto-1-methyl-1H-pyrazole-4-carboxylate (3) to 3-chloro-1-methyl-5-sulfamoyl pyrazole-4-carboxylate (4) under mild reaction conditions utilizing tetrabutyl ammonium chloride, N-chlorosuccinimide and ammonium carbonate (iii) condensation of sulphonamide (4) with carbamate (6) by microwave irradiation. Efforts were made to calculate, atom economy, reaction mass efficiency and E-factor for all the reaction steps involved in the synthesis of halosulfuron. The E-factor values in step 2 and step 4 reaction is lower, indicating that these reactions are greener (generation of less waste) when compared to the remaining steps in the synthesis.

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The development of an environmentally benign synthesis of sildenafil citrate (Viagra™) and its assessment by Green Chemistry metrics

Cited by 183 publications

References 5 publications

Tools and techniques for solvent selection: green solvent selection guides

Tools and techniques for solvent selection: green solvent selection guides

Mechanochemistry: opportunities for new and cleaner synthesis

Evaluation of Synthesis of Methyl 3-Chloro-5-(4,6-dimethoxypyrimidin- 2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate Using Green Metrics

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