Critical Assessment of Pharmaceutical ProcessesA Rationale for Changing the Synthetic Route

Butters, Michael; Catterick, David; Craig, Andrew; Curzons, Alan D.; Dale, David J.; Gillmore, Adam T.; Green, Stuart P.; Marziano, Ivan; Sherlock, Jon-Paul; White, W. Hunter

doi:10.1021/cr050982w

Cited by 202 publications

(151 citation statements)

References 56 publications

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“…[1][2][3] Burke's group has pioneered MIDA boronate chemistry, showing these compounds to be orthogonal to boronic acids in Suzuki-Miyaura (SM) reactions. By virtue of an sp The scope of MIDA boronates as protecting groups has been underlined in other related coupling reactions e.g.…”

Section: Introductionmentioning

confidence: 99%

Microwave-mediated synthesis of N-methyliminodiacetic acid (MIDA) boronates

Kemmitt

Emmerson

et al. 2014

Tetrahedron

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(2014) Microwavemediated synthesis of N-methyliminodiacetic acid (MIDA) boronates. Tetrahedron, 70 (47). pp. [9125][9126][9127][9128][9129][9130][9131] This version is available from Sussex Research Online: http://sro.sussex.ac.uk/53847/ This document is made available in accordance with publisher policies and may differ from the published version or from the version of record. If you wish to cite this item you are advised to consult the publisher's version. Please see the URL above for details on accessing the published version. Copyright and reuse:Sussex Research Online is a digital repository of the research output of the University.Copyright and all moral rights to the version of the paper presented here belong to the individual author(s) and/or other copyright owners. To the extent reasonable and practicable, the material made available in SRO has been checked for eligibility before being made available.Copies of full text items generally can be reproduced, displayed or performed and given to third parties in any format or medium for personal research or study, educational, or not-for-profit purposes without prior permission or charge, provided that the authors, title and full bibliographic details are credited, a hyperlink and/or URL is given for the original metadata page and the content is not changed in any way. ABSTRACT: A library of over twenty, mainly aryl or heteroaryl, N-methyliminodiacetic acid (MIDA) boronates has been synthesized. A rapid microwave-mediated (MW) method (5-10 mins) has been developed using polyethylene glycol 300 (PEG 300) as solvent. However, acetonitrile (MeCN) and dimethylformamide (DMF) were found to be alternative solvents, the latter especially for 2-substituted aryl boronic acids.

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Section: Introductionmentioning

confidence: 99%

Microwave-mediated synthesis of N-methyliminodiacetic acid (MIDA) boronates

Kemmitt

Emmerson

et al. 2014

Tetrahedron

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“…EI é a razão entre a energia utilizada e a massa do produto obtido e TI a razão entre o tempo utilizado e esta mesma massa. Como na indústria se procura maximizar a velocidade de obtenção do produto (throughput), um dos fatores mais importantes para o custo de produção, 57,58 para o seu cálculo exige-se o conhecimento do tempo das operações. Para permitir a obtenção destas métricas, as experiências incluíram a medição das energias e tempos ao longo dos procedimentos laboratoriais.…”

Section: Intensidade De Energia (Ei)unclassified

Extração Do R-(+)-Limoneno a Partir Das Cascas De Laranja: Avaliação E Otimização Da Verdura Dos Processos De Extração Tradicionais

Pires¹,

Ribeiro²,

Machado³

2017

Quim. Nova

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. This article reports a study, performed in educational context, to increase the greenness of the extraction of R-(+)-limonene from orange peels. Protocols from the literature were evaluated with the green star (GS) metric and new protocols, based in them, were designed to increase the overall greenness. These were tested in the laboratory and their greenness was assessed by traditional greenness metrics and metrics inspired in the industrial activity. Results showed that the steam distillation technique presents the largest overall greenness when evaluated by the GS, because organic solvents are not involved, but mass and energy metrics indicate that the extractions by solvent techniques are greener. This conflict denotes the complexity of the concept of chemical greenness and the need of using several types of metrics when greenness evaluation is at stake. The results show that the inclusion of experiments on the R-(+)-limonene extraction in the educational laboratory is efficient to show the difficulties of assessing the greenness of chemistry and of implementing Green Chemistry.Keywords: green metrics; green chemistry education; greenness improvement; limonene; orange oil. INTRODUÇÃOA escassez de recursos naturais e a ameaça de problemas ambientais, tanto a elevada produção de resíduos, muitos dos quais tóxicos, como os efeitos dos poluentes decorrentes da atividade humana, requerem modalidades inovadoras de implementação da química com menos impactos sobre o ambiente.1,2 Como consequência, nos últimos anos, observa-se um interesse crescente no uso de matérias-primas renováveis que possam ser uma alternativa aos recursos fósseis convencionais, contribuindo para a criação de um novo paradigma na indústria química, a bioindústria.1,3 A bioindústria inova relativamente à indústria convencional através da utilização de biomassa e respetivos resíduos como matéria-prima renovável, que é convertida em produtos comercializáveis através de tecnologias sustentáveis e de baixo impacto ambiental, em alternativa aos derivados de petróleo.1 A biomassa, sendo disponível em larga quantidade e renovável, merece presentemente muita e diversificada atenção como matéria-prima para a indústria química. [1][2][3][4][5][6] O termo bioindústria engloba as instalações da indústria química que usam biomassa como matéria-prima, havendo presentemente muito interesse em desenvolver e implementar um conceito mais amplo, de natureza sistémica, o de biorrefinaria. A biorrefinaria, analogamente a uma refinaria de petróleo que inclua instalações de indústria petroquímica, que produz vários combustíveis e substâncias a partir do petróleo, é um agrupamento de instalações de processos de conversão de biomassa em biocombustíveis, produtos químicos e energia, permitindo um maior aproveitamento da biomassa.1,7 Um exemplo de biorrefinaria é a produção de bioetanol, que pode ser usado quer como combustível, quer como reagente de base ("platform") no fabrico de outros produtos químicos.1,3 Atualmente, procura-se desenvolver biorrefinarias que utiliz...

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“…Thus, prompt discussions between the chemists and the chemical engineers provide both parties an early overview of what is possible, which problems have to be met, and which benchmarks have to be set. It is important to keep a holistic view of the benefits of each route [2]. Nonetheless, a change of the synthetic route will sometimes be necessary [2].…”

Section: General Aspectsmentioning

confidence: 99%

Comparison of Two Alternative Routes to an Enantiomerically Pure β‐Amino Acid

et al. 2010

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Enantiomerically pure b-amino acids are key building blocks for the synthesis of pharmaceuticals. Special consideration will be given to the production of (S)-3-aminobutanoic acid. Mass balancing is encouraged and highlighted to support the decision-making process in early stages of synthesis design when alternative routes are available. Though the overall yield of a chemical approach is twice as good as a chemoenzymatic route, the latter is more convincing regarding raw material consumption and costs as well as health issues. The energy flow analysis in early process development could not yet be carried out but principles concerning the modeling of energy demand were briefly exemplified by a comparative study of two processes with respect to decanoic acid methyl ester.

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Critical Assessment of Pharmaceutical ProcessesA Rationale for Changing the Synthetic Route

Cited by 202 publications

References 56 publications

Microwave-mediated synthesis of N-methyliminodiacetic acid (MIDA) boronates

Microwave-mediated synthesis of N-methyliminodiacetic acid (MIDA) boronates

Extração Do R-(+)-Limoneno a Partir Das Cascas De Laranja: Avaliação E Otimização Da Verdura Dos Processos De Extração Tradicionais

Comparison of Two Alternative Routes to an Enantiomerically Pure β‐Amino Acid

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