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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…mehr
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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WEI ZHANG, PHD, is Professor of Chemistry and Director of the Center for Green Chemistry at the University of Massachusetts Boston. He is known for research work in organic synthesis, medicinal chemistry, and green chemistry. He received the 2015 International Fluorous Technology Award and is one of the top three most published authors in fluorous chemistry. BERKELEY W. CUE, PHD, is President and Founder of BWC Pharma Consulting LLC, a consultancy specializing in pharmaceutical sciences and green chemistry, and Adjunct Professor of Chemistry at the University of Massachusetts Boston.
Inhaltsangabe
List of Contributors xvii Foreword xxi Preface xxiii Part I General Topics in Green Chemistry 1 Green ChemistryMetrics 3 Frank Roschangar and Juan Colberg 1.1 Business Case 3 1.2 Historical Context 3 1.3 Metrics, Awards, and Barriers 4 1.4 Metrics Unification Via Green Aspiration Level 9 1.5 Green Scorecard 12 1.6 Supply Chain 14 1.7 Outlook and Opportunities 15 References 17 Green Solvents 21 Janet L. Scott and Helen F. Sneddon 2.1 Introduction 21 2.2 Solvent Selection Guides and Tools 23 2.3 Greener Molecular Solvents 24 2.4 Opportunities, Challenges, and Future Developments 34 References 34 Green Analytical Chemistry 43 Paul Ferguson and Douglas Raynie 3.1 Introduction 43 3.2 Sample Preparation 47 3.3 Techniques and Methods 50 3.4 Process Analytical Technology 60 3.5 Biopharmaceutical Analysis 62 3.6 Conclusions 65 Acknowledgments 66 References 66 Green Engineering 71 Christopher L. Kitchens and Lindsay Soh 4.1 Introduction: Green Engineering Misconceptions and Realizations 71 4.2 12 Principles of Green Engineering 72 4.3 Green Chemistry Metrics Applied to Engineering 73 4.4 Use of Green Solvents in the Chemical Industry 80 4.5 Presidential Green Chemistry Awards 86 4.6 Opportunities and Outlook 87 References 87 Greening of Consumer Cleaning Products 91 David C. Long 5.1 History of Green Consumer Cleaning Products 91 5.2 Drivers for Greener Products 94 5.3 Development of Green Cleaning Criteria and Eco-Labeling 98 5.4 Development of Greener Ingredients for Cleaners 102 5.5 The Future of Green Cleaning 111 Acknowledgments 112 References 112 Innovation with Non-Covalent Derivatization 117 John C.Warner and Emily Stoler 6.1 Introduction 117 6.2 NCD Overview 118 6.3 Pharmaceutical NCDs 121 6.4 Environmental and Green Chemistry Benefits 123 References 123 Part II Green Catalysts 131 Catalytic C-H Bond Cleavage for Heterocyclic Compounds 133 Zhanxiang Liu and Yuhong Zhang 7.1 Introduction 133 7.2 Synthesis of Nitrogen Heterocycles 133 7.3 Synthesis of Oxygen-Containing Heterocycles 144 7.4 Synthesis of Sulfur-Containing Heterocycles 148 7.5 Medium-Sized Heterocyclic Compounds 150 7.6 Conclusion 152 References 152 Biocatalysis 161 James Lalonde 8.1 Introduction 161 8.2 Enzymes for Biocatalysis 162 8.3 Advances in Enzyme Engineering and Directed Evolution 164 8.4 Biocatalytic Synthesis of Pharmaceuticals: Case Studies of Highly Efficient Pharmaceutical Syntheses 165 8.5 Summary and Future Outlook 178 References 180 Practical Asymmetric Organocatalysis 185 Wen-Zhao Zhang, Samik Nanda, and Sanzhong Luo 9.1 Introduction 185 9.2 Aminocatalysis 185 9.3 Brønsted Acid Catalysis 191 9.4 Brønsted Base Catalysis 193 9.5 Hydrogen-Bonding Catalysis 197 9.6 Phase-Transfer Catalysis 202 9.7 Lewis Acid, Lewis Base, and N-Heterocyclic Carbene Catalysis 204 >100-Gram Reaction) 207 9.9 Conclusion 209 References 209 Fluorous Catalysis 219 L aszl o T. Mika and Istv an T. Horv ath 10.1 Introduction and the Principles of Fluorous Catalysis 219 10.2 Ligands for Fluorous Transition Metal Catalysts 224 10.3 Synthetic Application of Fluorous Catalysis 225 10.4 Fluorous Organocatalysis 256 10.5 Other Applications of Fluorous Catalysis 259 References 259 Solid-Supported Catalysis 269 Sukanta Bhattacharyya and Basudeb Basu 11.1 Introduction 269 11.2 Immobilized Palladium Catalysts 270 11.3 Immobilized Rhodium Catalysts 276 11.4 Immobilized Ruthenium Catalysts 279 11.5 Other Immobilized Catalysts 284 11.6 Conclusions 286 References 287 Asymmetric Organocatalysis in Aqueous Media 291 Kartick C. Bhowmick and Tanmoy Chanda 12.1 Introduction 291 12.2 Carbon-Carbon Bond-Formation Reactions 292 12.3 Reactions Other than C-C Bond Formation 313 12.4 Conclusion 314 References 314 Part III Green Synthetic Techniques 325 Solvent-Free Synthesis 327 Kendra Leahy Denlinger and JamesMack 13.1 Introduction 327 13.2 Ball Milling 328 References 339 Ultrasonic Reactions 343 Rodrigo Cella and H elio A. Stefani 14.1 Introduction 343 14.2 How Does CavitationWork? 343 14.3 Aldol/Condensation Reactions 345 14.4 1,4-Addition 351 14.5 Heterocycles Synthesis 353 14.6 Coupling Reactions 356 14.7 Wittig Reaction 361 14.8 Diels-Alder Reaction 362 14.9 Miscellaneous 365 14.10 Conclusions 366 References 366 Photochemical Synthesis 373 Stefano Protti,Maurizio Fagnoni, and Angelo Albini 15.1 Introduction 373 15.2 Synthesis and Rearrangement of Open-Chain Compounds 376 15.3 Synthesis of Three- and Four-Membered Rings 382 15.4 Synthesis of Five-, Six- (and Larger)-Membered Rings 391 15.5 Oxygenation and Oxidation 398 15.6 Conclusions 400 Acknowledgments 401 References 401 Pot Economy Synthesis 407 Wenbin Yi, Xin Zeng, and Song Gao 16.1 Introduction 407 16.2 Multicomponent Reactions 407 16.3 One-Pot and Multi-Step Reactions 415 16.4 One-Pot Asymmetric Synthesis 424 16.5 Outlook 434 References 434 Microwave-Assisted Organic Synthesis: Overview of Recent Applications 441 Nandini Sharma, Upendra K. Sharma, and Erik V. Van der Eycken 17.1 Introduction 441 17.2 C-H Functionalization 449 17.3 Insertion Reactions 452 17.4 Reduction 453 17.5 Synthesis of Peptides and Related Fine Chemicals 455 17.6 Newer Developments 459 17.7 Summary 461 References 461 Solid-Supported Synthesis 469 Indrajeet J. Barve and Chung-Ming Sun Abbreviations 469 18.1 Introduction 471 18.2 Techniques of Solid-Phase Supported Synthesis 472 18.3 Solid-Phase Supported Heterocyclic Chemistry 476 18.4 Solid-Supported Synthesis of Natural Products 486 18.5 Solid-Supported Organometallic Chemistry 491 18.6 Solid-Phase Synthesis of Peptides 493 18.7 Solid-Phase Supported Stereoselective Synthesis 494 18.8 Interdisciplinary Solid-Supported Synthesis 499 References 505 Light Fluorous Synthesis 509 Wei Zhang 19.1 Introduction 509 19.2 "Heavy" Versus "Light" Fluorous Chemistry 509 19.3 The Green Chemistry Aspects of Fluorous Synthesis 510 19.4 Fluorous Techniques for Discovery Chemistry 511 19.5 Conclusions 533 References 533 Part IV Green Techniques and Strategies in the Pharmaceutical Industry 539 Ionic Liquids in Pharmaceutical Industry 541 Julia L. Shamshina, Paula Berton, HuiWang, Xiaosi Zhou, Gabriela Gurau, and Robin D. Rogers Abbreviations 541 20.1 Introduction 543 20.2 Finding the Right Role for ILs in the Pharmaceutical Industry 544 20.3 Conclusions and Prospects 567 References 568 Green Technologies and Approaches in theManufacture of Biologics 579 Sa V. Ho and Kristi L. Budzinski 21.1 Introduction 579 21.2 Characteristics of Biologics 580 21.3 Manufacture of Therapeutic Biologics 581 21.4 Environmental Metrics Development and Impact Analysis 587 21.5 Some Future Directions 592 21.6 Conclusions 594 Acknowledgments 594 References 594 Benchmarking Green Chemistry Adoption by "Big Pharma"and Generics Manufacturers 601 Vesela R. Veleva and BerkeleyW. Cue 22.1 Introduction 601 22.2 Literature Review 602 22.3 Pharmaceutical Industry Overview and Green Chemistry Drivers 604 22.4 Benchmarking Industry Adoption of Green Chemistry 607 22.5 Results and Discussion 610 22.6 Conclusion 616 References 616 Green Process Chemistry in the Pharmaceutical Industry: Case Studies Update 621 Joseph M. Fortunak, Ji Zhang, Frederick E. Nytko III, and Tiffany N. Ellison 23.1 Introduction 621 23.2 Pharmaceutical Patents Driving Innovation 622 23.3 A Caution About Drug Manufacturing Costs 623 23.4 Process Evolution by Multiple Route Discovery Efforts-Dolutegravir 624 23.5 The Impact of Competition on Process Evolution-Tenofovir Disoproxil Fumarate 628 23.6 Simeprevir (Olysio/Sovriad) and Analogues: Chiral Phase-Transfer Catalyst-Promoted Optical Alpha-Amino Acid Synthesis: A Metal-free Process 633 23.7 Vaniprevir (MK 7009), Simeprevir (TMC435), and Danoprevir: Ring-Closing Metathesis (RCM) for Macrocyclic Lactam Synthesis: Now a Commercial Reality 635 23.8 Daclatasvir (BMS-790052, Daklinza), and Ledipasvir (GS-5885): Palladium Catalyzed Cross-Coupling for Greening a Process 638 23.9 Sitagliptin (Januvia) and Ponatinib (Iclusig): Greening the Process by Telescoping Multiple Steps Together 639 23.10 Febuxostat (Uloric): Greening the Process via Metal Catalyzed C-H Activation: A Prospect 641 23.11 Conclusions 644 References 644 Greener Pharmaceutical Science Through Collaboration: The ACS GCI Pharmaceutical Roundtable 649 Julie B. Manley andMichael E. Kopach 24.1 Introduction 649 24.2 Establishing Pre-Competitive Collaborations 650 24.3 Informing and Influencing the Research Agenda 654 24.4 Developing Tools 661 24.5 Educating Leaders 666 24.6 Collaborating Globally 668 24.7 Future Opportunities 669 24.8 Success Factors 671 References 673 Index 675
List of Contributors xvii Foreword xxi Preface xxiii Part I General Topics in Green Chemistry 1 Green ChemistryMetrics 3 Frank Roschangar and Juan Colberg 1.1 Business Case 3 1.2 Historical Context 3 1.3 Metrics, Awards, and Barriers 4 1.4 Metrics Unification Via Green Aspiration Level 9 1.5 Green Scorecard 12 1.6 Supply Chain 14 1.7 Outlook and Opportunities 15 References 17 Green Solvents 21 Janet L. Scott and Helen F. Sneddon 2.1 Introduction 21 2.2 Solvent Selection Guides and Tools 23 2.3 Greener Molecular Solvents 24 2.4 Opportunities, Challenges, and Future Developments 34 References 34 Green Analytical Chemistry 43 Paul Ferguson and Douglas Raynie 3.1 Introduction 43 3.2 Sample Preparation 47 3.3 Techniques and Methods 50 3.4 Process Analytical Technology 60 3.5 Biopharmaceutical Analysis 62 3.6 Conclusions 65 Acknowledgments 66 References 66 Green Engineering 71 Christopher L. Kitchens and Lindsay Soh 4.1 Introduction: Green Engineering Misconceptions and Realizations 71 4.2 12 Principles of Green Engineering 72 4.3 Green Chemistry Metrics Applied to Engineering 73 4.4 Use of Green Solvents in the Chemical Industry 80 4.5 Presidential Green Chemistry Awards 86 4.6 Opportunities and Outlook 87 References 87 Greening of Consumer Cleaning Products 91 David C. Long 5.1 History of Green Consumer Cleaning Products 91 5.2 Drivers for Greener Products 94 5.3 Development of Green Cleaning Criteria and Eco-Labeling 98 5.4 Development of Greener Ingredients for Cleaners 102 5.5 The Future of Green Cleaning 111 Acknowledgments 112 References 112 Innovation with Non-Covalent Derivatization 117 John C.Warner and Emily Stoler 6.1 Introduction 117 6.2 NCD Overview 118 6.3 Pharmaceutical NCDs 121 6.4 Environmental and Green Chemistry Benefits 123 References 123 Part II Green Catalysts 131 Catalytic C-H Bond Cleavage for Heterocyclic Compounds 133 Zhanxiang Liu and Yuhong Zhang 7.1 Introduction 133 7.2 Synthesis of Nitrogen Heterocycles 133 7.3 Synthesis of Oxygen-Containing Heterocycles 144 7.4 Synthesis of Sulfur-Containing Heterocycles 148 7.5 Medium-Sized Heterocyclic Compounds 150 7.6 Conclusion 152 References 152 Biocatalysis 161 James Lalonde 8.1 Introduction 161 8.2 Enzymes for Biocatalysis 162 8.3 Advances in Enzyme Engineering and Directed Evolution 164 8.4 Biocatalytic Synthesis of Pharmaceuticals: Case Studies of Highly Efficient Pharmaceutical Syntheses 165 8.5 Summary and Future Outlook 178 References 180 Practical Asymmetric Organocatalysis 185 Wen-Zhao Zhang, Samik Nanda, and Sanzhong Luo 9.1 Introduction 185 9.2 Aminocatalysis 185 9.3 Brønsted Acid Catalysis 191 9.4 Brønsted Base Catalysis 193 9.5 Hydrogen-Bonding Catalysis 197 9.6 Phase-Transfer Catalysis 202 9.7 Lewis Acid, Lewis Base, and N-Heterocyclic Carbene Catalysis 204 >100-Gram Reaction) 207 9.9 Conclusion 209 References 209 Fluorous Catalysis 219 L aszl o T. Mika and Istv an T. Horv ath 10.1 Introduction and the Principles of Fluorous Catalysis 219 10.2 Ligands for Fluorous Transition Metal Catalysts 224 10.3 Synthetic Application of Fluorous Catalysis 225 10.4 Fluorous Organocatalysis 256 10.5 Other Applications of Fluorous Catalysis 259 References 259 Solid-Supported Catalysis 269 Sukanta Bhattacharyya and Basudeb Basu 11.1 Introduction 269 11.2 Immobilized Palladium Catalysts 270 11.3 Immobilized Rhodium Catalysts 276 11.4 Immobilized Ruthenium Catalysts 279 11.5 Other Immobilized Catalysts 284 11.6 Conclusions 286 References 287 Asymmetric Organocatalysis in Aqueous Media 291 Kartick C. Bhowmick and Tanmoy Chanda 12.1 Introduction 291 12.2 Carbon-Carbon Bond-Formation Reactions 292 12.3 Reactions Other than C-C Bond Formation 313 12.4 Conclusion 314 References 314 Part III Green Synthetic Techniques 325 Solvent-Free Synthesis 327 Kendra Leahy Denlinger and JamesMack 13.1 Introduction 327 13.2 Ball Milling 328 References 339 Ultrasonic Reactions 343 Rodrigo Cella and H elio A. Stefani 14.1 Introduction 343 14.2 How Does CavitationWork? 343 14.3 Aldol/Condensation Reactions 345 14.4 1,4-Addition 351 14.5 Heterocycles Synthesis 353 14.6 Coupling Reactions 356 14.7 Wittig Reaction 361 14.8 Diels-Alder Reaction 362 14.9 Miscellaneous 365 14.10 Conclusions 366 References 366 Photochemical Synthesis 373 Stefano Protti,Maurizio Fagnoni, and Angelo Albini 15.1 Introduction 373 15.2 Synthesis and Rearrangement of Open-Chain Compounds 376 15.3 Synthesis of Three- and Four-Membered Rings 382 15.4 Synthesis of Five-, Six- (and Larger)-Membered Rings 391 15.5 Oxygenation and Oxidation 398 15.6 Conclusions 400 Acknowledgments 401 References 401 Pot Economy Synthesis 407 Wenbin Yi, Xin Zeng, and Song Gao 16.1 Introduction 407 16.2 Multicomponent Reactions 407 16.3 One-Pot and Multi-Step Reactions 415 16.4 One-Pot Asymmetric Synthesis 424 16.5 Outlook 434 References 434 Microwave-Assisted Organic Synthesis: Overview of Recent Applications 441 Nandini Sharma, Upendra K. Sharma, and Erik V. Van der Eycken 17.1 Introduction 441 17.2 C-H Functionalization 449 17.3 Insertion Reactions 452 17.4 Reduction 453 17.5 Synthesis of Peptides and Related Fine Chemicals 455 17.6 Newer Developments 459 17.7 Summary 461 References 461 Solid-Supported Synthesis 469 Indrajeet J. Barve and Chung-Ming Sun Abbreviations 469 18.1 Introduction 471 18.2 Techniques of Solid-Phase Supported Synthesis 472 18.3 Solid-Phase Supported Heterocyclic Chemistry 476 18.4 Solid-Supported Synthesis of Natural Products 486 18.5 Solid-Supported Organometallic Chemistry 491 18.6 Solid-Phase Synthesis of Peptides 493 18.7 Solid-Phase Supported Stereoselective Synthesis 494 18.8 Interdisciplinary Solid-Supported Synthesis 499 References 505 Light Fluorous Synthesis 509 Wei Zhang 19.1 Introduction 509 19.2 "Heavy" Versus "Light" Fluorous Chemistry 509 19.3 The Green Chemistry Aspects of Fluorous Synthesis 510 19.4 Fluorous Techniques for Discovery Chemistry 511 19.5 Conclusions 533 References 533 Part IV Green Techniques and Strategies in the Pharmaceutical Industry 539 Ionic Liquids in Pharmaceutical Industry 541 Julia L. Shamshina, Paula Berton, HuiWang, Xiaosi Zhou, Gabriela Gurau, and Robin D. Rogers Abbreviations 541 20.1 Introduction 543 20.2 Finding the Right Role for ILs in the Pharmaceutical Industry 544 20.3 Conclusions and Prospects 567 References 568 Green Technologies and Approaches in theManufacture of Biologics 579 Sa V. Ho and Kristi L. Budzinski 21.1 Introduction 579 21.2 Characteristics of Biologics 580 21.3 Manufacture of Therapeutic Biologics 581 21.4 Environmental Metrics Development and Impact Analysis 587 21.5 Some Future Directions 592 21.6 Conclusions 594 Acknowledgments 594 References 594 Benchmarking Green Chemistry Adoption by "Big Pharma"and Generics Manufacturers 601 Vesela R. Veleva and BerkeleyW. Cue 22.1 Introduction 601 22.2 Literature Review 602 22.3 Pharmaceutical Industry Overview and Green Chemistry Drivers 604 22.4 Benchmarking Industry Adoption of Green Chemistry 607 22.5 Results and Discussion 610 22.6 Conclusion 616 References 616 Green Process Chemistry in the Pharmaceutical Industry: Case Studies Update 621 Joseph M. Fortunak, Ji Zhang, Frederick E. Nytko III, and Tiffany N. Ellison 23.1 Introduction 621 23.2 Pharmaceutical Patents Driving Innovation 622 23.3 A Caution About Drug Manufacturing Costs 623 23.4 Process Evolution by Multiple Route Discovery Efforts-Dolutegravir 624 23.5 The Impact of Competition on Process Evolution-Tenofovir Disoproxil Fumarate 628 23.6 Simeprevir (Olysio/Sovriad) and Analogues: Chiral Phase-Transfer Catalyst-Promoted Optical Alpha-Amino Acid Synthesis: A Metal-free Process 633 23.7 Vaniprevir (MK 7009), Simeprevir (TMC435), and Danoprevir: Ring-Closing Metathesis (RCM) for Macrocyclic Lactam Synthesis: Now a Commercial Reality 635 23.8 Daclatasvir (BMS-790052, Daklinza), and Ledipasvir (GS-5885): Palladium Catalyzed Cross-Coupling for Greening a Process 638 23.9 Sitagliptin (Januvia) and Ponatinib (Iclusig): Greening the Process by Telescoping Multiple Steps Together 639 23.10 Febuxostat (Uloric): Greening the Process via Metal Catalyzed C-H Activation: A Prospect 641 23.11 Conclusions 644 References 644 Greener Pharmaceutical Science Through Collaboration: The ACS GCI Pharmaceutical Roundtable 649 Julie B. Manley andMichael E. Kopach 24.1 Introduction 649 24.2 Establishing Pre-Competitive Collaborations 650 24.3 Informing and Influencing the Research Agenda 654 24.4 Developing Tools 661 24.5 Educating Leaders 666 24.6 Collaborating Globally 668 24.7 Future Opportunities 669 24.8 Success Factors 671 References 673 Index 675
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