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- Herausgeber: John Wiley & Sons
- Kategorie: Wissenschaft und neue Technologien
- Sprache: Englisch
An updated overview of the rapidly developing field of green techniques for organic synthesis and medicinal chemistry
Green chemistry remains a high priority in modern organic synthesis and pharmaceutical R&D, with important environmental and economic implications. This book presents comprehensive coverage of green chemistry techniques for organic and medicinal chemistry applications, summarizing the available new technologies, analyzing each technique’s features and green chemistry characteristics, and providing examples to demonstrate applications for green organic synthesis and medicinal chemistry.
The extensively revised edition of Green Techniques for Organic Synthesis and Medicinal Chemistry includes 7 entirely new chapters on topics including green chemistry and innovation, green chemistry metrics, green chemistry and biological drugs, and the business case for green chemistry in the generic pharmaceutical industry. It is divided into 4 parts. The first part introduces readers to the concepts of green chemistry and green engineering, global environmental regulations, green analytical chemistry, green solvents, and green chemistry metrics. The other three sections cover green catalysis, green synthetic techniques, and green techniques and strategies in the pharmaceutical industry.
- Includes more than 30% new and updated material—plus seven brand new chapters
- Edited by highly regarded experts in the field (Berkeley Cue is one of the fathers of Green Chemistry in Pharma) with backgrounds in academia and industry
- Brings together a team of international authors from academia, industry, government agencies, and consultancies (including John Warner, one of the founders of the field of Green Chemistry)
Green Techniques for Organic Synthesis and Medicinal Chemistry, Second Edition is an essential resource on green chemistry technologies for academic researchers, R&D professionals, and students working in organic chemistry and medicinal chemistry.
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Veröffentlichungsjahr: 2018
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Green Techniques for Organic Synthesis and Medicinal Chemistry
Edited by
Wei Zhang
Department of Chemistry University of Massachusetts-Boston Massachusetts USA
BerkeleyW. Cue
BWC Pharma Consulting Nottingham, New Hampshire USA
Second Edition
This edition first published 2018 © 2018 John Wiley & Sons Ltd
All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, except as permitted by law. Advice on how to obtain permission to reuse material from this title is available at http://www.wiley.com/go/permissions.
The right of Wei Zhang and Berkeley W. Cue to be identified as the authors of the editorial material in this work has been asserted in accordance with law.
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Limit of Liability/Disclaimer of WarrantyIn view of ongoing research, equipment modifications, changes in governmental regulations, and the constant flow of information relating to the use of experimental reagents, equipment, and devices, the reader is urged to review and evaluate the information provided in the package insert or instructions for each chemical, piece of equipment, reagent, or device for, among other things, any changes in the instructions or indication of usage and for added warnings and precautions. While the publisher and authors have used their best efforts in preparing this work, they make no representations or warranties with respect to the accuracy or completeness of the contents of this work and specifically disclaim all warranties, including without limitation any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives, written sales materials or promotional statements for this work. The fact that an organization, website, or product is referred to in this work as a citation and/or potential source of further information does not mean that the publisher and authors endorse the information or services the organization, website, or product may provide or recommendations it may make. This work is sold with the understanding that the publisher is not engaged in rendering professional services. The advice and strategies contained herein may not be suitable for your situation. You should consult with a specialist where appropriate. Further, readers should be aware that websites listed in this work may have changed or disappeared between when this work was written and when it is read. Neither the publisher nor authors shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages.
Library of Congress Cataloging-in-Publication Data
Names: Zhang, Wei, 1961– editor. | Cue, Berkeley W., editor. Title: Green techniques for organic synthesis and medicinal chemistry / edited by Wei Zhang, Berkeley W. Cue, Jr. Description: Second edition. | Hoboken, NJ : John Wiley & Sons, 2018. | Includes index. | Identifiers: LCCN 2017043086 (print) | LCCN 2017047560 (ebook) | ISBN 9781119288176 (pdf) | ISBN 9781119288589 (epub) | ISBN 9781119288169 (cloth) Subjects: LCSH: Pharmaceutical chemistry. | Green chemistry. Classification: LCC RS403 (ebook) | LCC RS403 .G74 2018 (print) | DDC 615.1/9--dc23 LC record available at https://lccn.loc.gov/2017043086
Cover Design: Wiley Cover Images: (top) © blueclue/Getty Images; (bottom) © funnyangel/Shutterstock
CONTENTS
List of Contributors
Foreword
Preface
Part I General Topics in Green Chemistry
1 Green Chemistry Metrics
1.1 Business Case
1.2 Historical Context
1.3 Metrics, Awards, and Barriers
1.4 Metrics Unification Via Green Aspiration Level
1.5 Green Scorecard
1.6 Supply Chain
1.7 Outlook and Opportunities
References
2 Green Solvents
2.1 Introduction
2.2 Solvent Selection Guides and Tools
2.3 Greener Molecular Solvents
2.4 Opportunities, Challenges, and Future Developments
References
3 Green Analytical Chemistry
3.1 Introduction
3.2 Sample Preparation
3.3 Techniques and Methods
3.4 Process Analytical Technology
3.5 Biopharmaceutical Analysis
3.6 Conclusions
Acknowledgments
References
4 Green Engineering
4.1 Introduction: Green Engineering Misconceptions and Realizations
4.2 12 Principles of Green Engineering
4.3 Green Chemistry Metrics Applied to Engineering
4.4 Use of Green Solvents in the Chemical Industry
4.5 Presidential Green Chemistry Awards
4.6 Opportunities and Outlook
References
5 Greening of Consumer Cleaning Products
5.1 History of Green Consumer Cleaning Products
5.2 Drivers for Greener Products
5.3 Development of Green Cleaning Criteria and Eco-Labeling
5.4 Development of Greener Ingredients for Cleaners
5.5 The Future of Green Cleaning
Acknowledgments
References
6 Innovation with Non-Covalent Derivatization
6.1 Introduction
6.2 NCD Overview
6.3 Pharmaceutical NCDs
6.4 Environmental and Green Chemistry Benefits
References
Part II Green Catalysts
7 Catalytic C-H Bond Cleavage for Heterocyclic Compounds
7.1 Introduction
7.2 Synthesis of Nitrogen Heterocycles
7.3 Synthesis of Oxygen-Containing Heterocycles
7.4 Synthesis of Sulfur-Containing Heterocycles
7.5 Medium-Sized Heterocyclic Compounds
7.6 Conclusion
References
8 Biocatalysis
8.1 Introduction
8.2 Enzymes for Biocatalysis
8.3 Advances in Enzyme Engineering and Directed Evolution
8.4 Biocatalytic Synthesis of Pharmaceuticals: Case Studies of Highly Efficient Pharmaceutical Syntheses
8.5 Summary and Future Outlook
References
9 Practical Asymmetric Organocatalysis
9.1 Introduction
9.2 Aminocatalysis
9.3 Brønsted Acid Catalysis
9.4 Brønsted Base Catalysis
9.5 Hydrogen-Bonding Catalysis
9.6 Phase-Transfer Catalysis
9.7 Lewis Acid, Lewis Base, and
N
-Heterocyclic Carbene Catalysis
9.8 Large-Scale Reaction (>100-Gram Reaction)
9.9 Conclusion
References
10 Fluorous Catalysis
10.1 Introduction and the Principles of Fluorous Catalysis
10.2 Ligands for Fluorous Transition Metal Catalysts
10.3 Synthetic Application of Fluorous Catalysis
10.4 Fluorous Organocatalysis
10.5 Other Applications of Fluorous Catalysis
References
11 Solid-Supported Catalysis
11.1 Introduction
11.2 Immobilized Palladium Catalysts
11.3 Immobilized Rhodium Catalysts
11.4 Immobilized Ruthenium Catalysts
11.5 Other Immobilized Catalysts
11.6 Conclusions
References
12 Asymmetric Organocatalysis in Aqueous Media
12.1 Introduction
12.2 Carbon-Carbon Bond-Formation Reactions
12.3 Reactions Other than C-C Bond Formation
12.4 Conclusion
References
Part III Green Synthetic Techniques
13 Solvent-Free Synthesis
13.1 Introduction
13.2 Ball Milling
References
14 Ultrasonic Reactions
14.1 Introduction
14.2 How Does Cavitation Work?
14.3 Aldol/Condensation Reactions
14.4 1,4-Addition
14.5 Heterocycles Synthesis
14.6 Coupling Reactions
14.7 Wittig Reaction
14.8 Diels-Alder Reaction
14.9 Miscellaneous
14.10 Conclusions
References
15 Photochemical Synthesis
15.1 Introduction
15.2 Synthesis and Rearrangement of Open-Chain Compounds
15.3 Synthesis of Three- and Four-Membered Rings
15.4 Synthesis of Five-, Six- (and Larger)-Membered Rings
15.5 Oxygenation and Oxidation
15.6 Conclusions
Acknowledgments
References
16 Pot Economy Synthesis
16.1 Introduction
16.2 Multicomponent Reactions
16.3 One-Pot and Multi-Step Reactions
16.4 One-Pot Asymmetric Synthesis
16.5 Outlook
References
17 Microwave-Assisted Organic Synthesis: Overview of Recent Applications
17.1 Introduction
17.2 C-H Functionalization
17.3 Insertion Reactions
17.4 Reduction
17.5 Synthesis of Peptides and Related Fine Chemicals
17.6 Newer Developments
17.7 Summary
References
18 Solid-Supported Synthesis
Abbreviations
18.1 Introduction
18.2 Techniques of Solid-Phase Supported Synthesis
18.3 Solid-Phase Supported Heterocyclic Chemistry
18.4 Solid-Supported Synthesis of Natural Products
18.5 Solid-Supported Organometallic Chemistry
18.6 Solid-Phase Synthesis of Peptides
18.7 Solid-Phase Supported Stereoselective Synthesis
18.8 Interdisciplinary Solid-Supported Synthesis
References
19 Light Fluorous Synthesis
19.1 Introduction
19.2 “Heavy” Versus “Light” Fluorous Chemistry
19.3 The Green Chemistry Aspects of Fluorous Synthesis
19.4 Fluorous Techniques for Discovery Chemistry
19.5 Conclusions
References
Part IV Green Techniques and Strategies in the Pharmaceutical Industry
20 Ionic Liquids in Pharmaceutical Industry
Abbreviations
20.1 Introduction
20.2 Finding the Right Role for ILs in the Pharmaceutical Industry
20.3 Conclusions and Prospects
References
21 Green Technologies and Approaches in the Manufacture of Biologics
21.1 Introduction
21.2 Characteristics of Biologics
21.3 Manufacture of Therapeutic Biologics
21.4 Environmental Metrics Development and Impact Analysis
21.5 Some Future Directions
21.6 Conclusions
Acknowledgments
References
22 Benchmarking Green Chemistry Adoption by “Big Pharma” and Generics Manufacturers [1]
22.1 Introduction
22.2 Literature Review
22.3 Pharmaceutical Industry Overview and Green Chemistry Drivers
22.4 Benchmarking Industry Adoption of Green Chemistry
22.5 Results and Discussion
22.6 Conclusion
References
23 Green Process Chemistry in the Pharmaceutical Industry: Case Studies Update (2012–2016)
23.1 Introduction
23.2 Pharmaceutical Patents Driving Innovation
23.3 A Caution About Drug Manufacturing Costs
23.4 Process Evolution by Multiple Route Discovery Efforts—Dolutegravir
23.5 The Impact of Competition on Process Evolution—Tenofovir Disoproxil Fumarate
23.6 Simeprevir (Olysio/Sovriad) and Analogues: Chiral Phase-Transfer Catalyst-Promoted Optical Alpha-Amino Acid Synthesis: A Metal-free Process
23.7 Vaniprevir (MK 7009), Simeprevir (TMC435), and Danoprevir: Ring-Closing Metathesis (RCM) for Macrocyclic Lactam Synthesis: Now a Commercial Reality
23.8 Daclatasvir (BMS-790052, Daklinza), and Ledipasvir (GS-5885): Palladium Catalyzed Cross-Coupling for Greening a Process
23.9 Sitagliptin (Januvia) and Ponatinib (Iclusig): Greening the Process by Telescoping Multiple Steps Together
23.10 Febuxostat (Uloric): Greening the Process via Metal Catalyzed C-H Activation: A Prospect
23.11 Conclusions
References
24 Greener Pharmaceutical Science Through Collaboration: The ACS GCI Pharmaceutical Roundtable
24.1 Introduction
24.2 Establishing Pre-Competitive Collaborations
24.3 Informing and Influencing the Research Agenda
24.4 Developing Tools
24.5 Educating Leaders
24.6 Collaborating Globally
24.7 Future Opportunities
24.8 Success Factors
References
Index
EULA
List of Tables
Chapter 1
Table 1.1
Table 1.2
Table 1.3
Table 1.4
Table 1.5
Table 1.6
Chapter 2
Table 2.1
Chapter 3
Table 3.1
Table 3.2
Chapter 4
Table 4.1
Table 4.2
Table 4.3
Chapter 5
Table 5.1
Chapter 8
Table 8.1
Chapter 10
Table 10.1
Table 10.2
Table 10.3
Table 10.4
Table 10.5
Chapter 13
Table 13.1
Table 13.2
Chapter 14
Table 14.1
Table 14.2
Table 14.3
Table 14.4
Table 14.5
Chapter 19
Table 19.1
Table 19.2
Table 19.3
Table 19.4
Table 19.5
Table 19.6
Chapter 20
Table 20.1
Table 20.2
Table 20.3
Chapter 21
Table 21.1
Table 21.2
Table 21.3
Chapter 22
Table 22.1
Table 22.2
Table 22.3
Chapter 23
Table 23.1
Chapter 24
Table 24.1
Table 24.2
Table 24.3
Table 24.4
Guide
Cover
Table of Contents
Preface
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