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Green Techniques for Organic Synthesis and Medicinal Chemistry
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Green Techniques for Organic Synthesis and Medicinal Chemistry

Zhang, Wei; Cue, Berkeley
ISBN-10: 0470711515
ISBN-13: 9780470711514

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Green chemistry is rapidly becoming a high priority in modern organic synthesis and pharmaceutical R&D, but there is currently no green chemistry book which addresses both organic synthesis and medicinal chemistry.  This book presents updated and comprehensive coverage of green chemistry technologies for organic and medicinal chemistry applications.
The book is divided into 4 parts:Part I - an introduction to the toxicology of organic chemicals and the concept of green organic synthesis.Part II - covers catalysis, the most important and active topic in green chemistry. Part III - introduces a series of new techniques, including atom economic multicomponent reactions; alternative energy microwave and ultrasound for reactions; solid-phase, fluorous and ionic liquid-based recycling techniques; solvent-free ball milling; and solvent-less microfluidic devices. The green chemistry aspects and limitations (i.e. cost, equipment, expertise) of each technique will be assessed.Part IV – covers applications of green chemistry concepts and special techniques for medicinal chemistry applications including synthesis, analysis, separation, formulation, toxicology, and drug delivery. The book concludes with case studies, illustrating practical applications in the pharmaceutical industry.
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List of Contributors
Introduction
Green Toxicology
Introduction
History and Scope of Toxicology
The need for green toxicology
Principles of Toxicology
Characteristics of exposure
Spectrum of toxic effects
The dose-response relationship
Disposition of Toxicants in Organisms
Absorption
Distribution
Metabolism
Excretion
Nonorgan System Toxicity
Carcinogenesis
Reproductive and developmental toxicity
Immunotoxicology
Mechanistic Toxicology
Quantitative Structure-Activity Relationships
Environmental Toxicology
Persistence and bioaccumulation
Risk Assessment
NonCancer risk assessment
Cancer risk assessment
Conclusions
References
Green Chemistry and the Pharmaceutical Industry
Introduction
Green Chemistry versus Sustainable Chemistry
Trend: The Ongoing Use of Hazardous Chemistry
Myth: To Do Green Chemistry One Must Sacrifice Performance and Cost
Green Chemistry and the Future of the Pharmaceutical Industry
Green Chemistry in Pharmaceutical Process Development and Manufacturing
Conclusions
References
Green Catalysis
Environmental Science and Green Chemistry; Guiding Environmentally Preferred Manufacturing, Materials, and Products
Introduction
Market Forces
Chemicals in the natural and human environment
Precautionary decision making
Chemical control laws
Green chemistry initiatives
Drug registration Environmental Risk Assessment (ERA)
Extended Producer Responsibility (EPR)
Ecosystem valuation
Company expectations
Public expectations
Environmental labeling, standards, and classification
Indicators (Attributes) of Environmental Performance
Environmental Impact
Strategic Approach to Greener Manufacturing Processes and Products
Manufacturing Process Improvements
Business and Professional Advantages from Manufacturing Process Improvements
Product Improvements
Environmental Decision Making
E-factor
Process Mass Intensity (PMI)
Life Cycle Assessment (LCA)
Individual company initiatives
Environmental (Ecological) Risk Assessment (ERA)
Alternatives Assessment (AA)/Chemical Alternatives Assessment (CAA)
Green Screen
iSUSTAINTM Green chemistry index
Computational Science and Quantitative Structure-Activity Relationships (QSARs)
Tiered testing
Databases and lists of chemicals
Case Study - Pharmaceuticals/Biologics
Pharmaceutical manufacturing
Pharmaceutical products
Case Study - Nanotechnology
Green Credentials and Environmental Standards
Inspiring Innovation - Academic and Industry Programs
Academic programs
Industry programs
Conclusions and Recommendations
References
Direct CH Bond Activation Reactions
Introduction
Homogeneous CH Activation by Metal Complex Catalysis
Pd-catalyzed carbon-carbon bond formations
Pd-catalyzed carbon-heteroatom bond formation
CH activation by other metals
Heterogeneous Catalytic Methods for CH Activation
Supported metal complexes
Supported metals
CH Activation by Organocatalysts
Enzymatic CH Activations
References
Supported Asymmetric Organocatalysis
Introduction
Polymer-Supported Organocatalysts
Polymer-supported chiral amines for enamine and iminiun catalysis
Polymer-supported phase transfer catalysts
Polymer-supported phosphoric acid catalyst
Miscellaneous
Solid Acid-Supported Organocatalysis
Polyoxometalate-supported chiral amine catalysts
Solid sulfonic acid supported chiral amine catalysts
Ionic Liquid-Supported Organocatalysts
Magnetic Nanoparticle-Supported Organocatalysts
Silica-Supported Asymmetric Organocatalysts
Silica-supported proline and its derivatives
Silica-supported MacMillan catalysts
Other silica-supported organocatalysts
Clay Entrapped Organocatalysts
Miscellaneous
Conclusion
Acknowledgments
References
Fluorous Catalysis
Introduction and the Principles of Fluorous Catalysis
Ligands for Fluorous Transition Metal Catalysts
Synthetic Application of Fluorous Catalysis
Hydroformylation
Hydrogenation
Hydrosylilation
Cross-coupling reactions
Hydroboration
Oxidation
Esterification, transesterification and acetylation
Other metal catalyzed carbon-carbon bond forming reactions
Fluorous Organocatalysis
References
Solid-Supported Catalysis
Introduction
General Introduction
The impact of solid-phase organic synthesis on green chemistry
Immobilized Palladium Catalysts for Green Chemistry
Introduction
Suzuki reactions
Heck-Mizoroki reactions in water
Sonogashira reactions in water
Tsuji-Trost reactions in water
Immobilized Rhodium Catalysts for Green Chemistry
Introduction
Rhodium(II) carbenoid chemistry
Rhodium (I)-catalyzed conjugate addition reactions
Rhodium-catalyzed hydrogenation reactions
Rhodium-catalyzed carbonylation reactions
Immobilized Ruthenium Catalysts for Green Chemistry
Introduction
Ruthenium-catalyzed metathesis reactions
Ruthenium-catalyzed transfer hydrogenation
Ruthenium-catalyzed opening of epoxides
Ruthenium-catalyzed cyclopropanation reactions
Ruthenium-catalyzed halogenation reactions
Other Immobilized Catalysts for Green Chemistry
Immobilized cobalt catalysts
Immobilized copper catalysts
Immobilized iridium catalysts
Conclusions
References
Biocatalysis
Introduction
Brief History of Biocatalysis
Biocatalysis Toolboxes
Enzymatic Synthesis of Pharmaceuticals
Synthesis of atorvastatin and rosuvastatin
Synthesis of b-lactam antibiotics
Synthesis of glycopeptides
Synthesis of tyrocidine antibiotics
Synthesis of polyketides
Synthesis of taxoids and epothilones
Synthesis of pregabalin
Summary
Acknowledgment
References
Green Synthetic Techniques
Green Solvents
Introduction
Origins of the Neoteric Solvents
Ionic liquids
Supercritical carbon dioxide
Water
Perfluorinated solvents
Biosolvents
Petroleum solvents
Application of Green Solvents
Synthetic organic chemistry overview
Diels-Alder cycloaddition
Cross-coupling
Ring-closing metathesis
Recapitulation and Possible Future Developments
References
Organic Synthesis in Water
Introduction
Pericyclic Reactions
Passerini and Ugi Reactions
Nucleophilic Ring-Opening Reactions
Transition Metal Catalyzed Reactions
Pericyclic reactions
Addition reactions
Coupling reactions
Transition metal catalyzed reactions of carbenes
Oxidations and reductions
Organocatalytic Reactions
Aldol reaction
Michael addition
Mannich reaction
Cycloaddition reactions
Miscellaneous
Conclusion
References
Solvent-Free Synthesis
Introduction
Alternative Methods to Solution Based Synthesis
Mortar and pestle
Ball milling
Microwave assisted solvent-free synthesis
References
Microwave Synthesis
Introduction
The Mechanism of Microwave Heating
The Green Properties of Microwave Heating
Green solvents
Energy reduction
Improved reaction outcomes resulting in less purification
Microwaves versus Green Chemistry Principles
Green Solvents in Microwave Chemistry
Water
Solventless reactions
Ionic liquids
Glycerol
Catalysis
Microwave assisted CH bond activation
Microwave assisted carbonylation reactions
Microwave Chemistry Scale-Up
Flow microwave reactors
Energy efficiency of large-scale microwave reactions
Large-scale batch microwave reactors
Future work in microwave scale-up
Summary
References
Ultrasonic Reactions
Introduction
How Does Cavitation Work?
Condensation Reactions
Michael Additions
Mannich Reactions
Heterocycles Synthesis
Coupling Reactions
Miscellaneous
Conclusions
References
Photochemical Synthesis
Introduction
Synthesis and Rearrangement of Open-Chain Compounds
Synthesis of Three- and Four-Membered Rings
Synthesis of three-membered rings
Synthesis of four-membered rings
Synthesis of Five-, Six (and Larger)-Membered Rings
Synthesis of five-membered rings
Synthesis of six-membered rings
Synthesis of larger rings
Oxygenation and Oxidation
Conclusions
Acknowledgment
References
Solid-Supported Organic Synthesis
Introduction
Techniques of Solid-Supported Synthesis
General method of solid-supported synthesis
Supports for supported synthesis
Linkers for solid-supported synthesis
Reaction monitoring
Separation techniques
Automation technique
Split and combine (split and mix) technique
Solid-Supported Heterocyclic Chemistry
Multicomponent reaction
Combinatorial library synthesis
Diversity-oriented synthesis
Multistep parallel synthesis
Solid-Supported Natural Product Synthesis
Total synthesis of natural product
Synthesis of natural product-like libraries
Synthesis of natural product inspired compounds
Solid-Supported Synthesis of Peptides and Carbohydrates
Solid-supported synthesis of peptides
Solid-supported synthesis of carbohydrates
Soluble-Supported Synthesis
Poly(ethylene glycol)
Linear polystyrene (LPS)
Ionic liquids
Multidisciplinary Synthetic Approaches
Solid-supported synthesis and microwave synthesis
Solid-supported synthesis under sonication
Solid-supported synthesis in green media
Solid-supported synthesis and photochemical reactions
References
Fluorous Synthesis
Introduction
"Heavy" versus "Light" Fluorous Chemistry
Green Aspects of Fluorous Techniques
Fluorous solid-phase extraction to reduce the amount of waste solvent
Recycling techniques in fluorous synthesis
Monitoring fluorous reactions
Two-in-one strategy for using fluorous linkers
Efficient microwave-assisted fluorous synthesis
Atom economic fluorous multicomponent reactions
Fluorous reactions and separations in aqueous media
Fluorous Techniques for Discovery Chemistry
Fluorous ligands for metal catalysis
Fluorous organocatalysts for asymmetric synthesis
Fluorous reagents
Fluorous scavengers
Fluorous linkers
Conclusions
References
Reactions in Ionic Liquids
Introduction
Finding the Right Role for ILs in the Pharmaceutical Industry
Use of ILs as solvents in the synthesis of drugs or drug intermediates
Use of ILs for pharmaceutical crystallization
Use of ILs in pharmaceutical separations
Use of ILs for the extraction of drugs from natural products
Use of ILs for drug delivery
Use of ILs for drug detection
ILs as pharmaceutical ingredients
Conclusions and Prospects
References
Multicomponent Reactions
Introduction
Multicomponent Reactions in Aqueous Medium
Multicomponent reactions are accelerated in water
Multicomponent reactions "on water"
Solventless Multicomponent Reactions
Case Studies of Multicomponent Reactions in Drug Synthesis
Schistosomiasis drug praziquantel
Schizophrenia drug olanzapine
Oxytocin antagonist GSK221149A
Miscellaneous
Perspectives of Multicomponent Reactions in Green Chemistry
The union of multicomponent reactions
Sustainable synthesis technology by multicomponent reactions
Alternative solvents for green chemistry
Outlook
References
Flow Chemistry
Introduction
Types of Flow Reactors
Microreactors
Miniaturized tubular reactors
Spinning Disk Reactor (SDR)
Spinning tube-in-tube reactor
Heat exchanger reactors
Application of Flow Reactors
Prevention of waste and yield improvement
Increase energy efficiency and minimize potential for accidents
Use of heterogeneous catalysts and atom efficiency
Use of supported reagents
Photochemistry
Conclusion
Acknowledgment
References
Green Chemistry Strategies for Medicinal Chemists
Introduction
Historical Background: The Evolution of Green Chemistry in the Pharmaceutical Industry
Green Chemistry in Process Chemistry, Manufacturing and Medicinal Chemistry and Barriers to Rapid Uptake
Green Chemistry Activity Among PhRMA Member Companies
Modeling Waste Generation in Pharmaceutical R&D
Strategies to Reduce the Use of Solvents
Green Reactions for Medicinal Chemistry
Modeling Waste Co-Produced During R&D Synthesis
Green Chemistry and Drug Design: Benign by Design
Green Biology
Conclusions and Recommendations
References
Green Techniques For Medicinal Chemistry
The Business of Green Chemistry in the Pharmaceutical Industry
Introduction
Green Chemistry as a Business Opportunity
The Need for Green Chemistry
The Business Case for Green Chemistry Principles
An Idea whose Time Has Arrived
What Green Chemistry Is and What It Is Not
Overcoming Obstacles to Green Chemistry
Conclusion
References
Preparative Chromatography
Introduction
Preparative Chromatography for Intermediates and APIs
Early discovery
Clinical and commercial scale quantities
Chiral separations
Chromatography and the
12. Principles of Green Chemistry
The
12. principles
The metrics
The impact of chromatography on the environment
Overview of Chromatography Systems
Chromatographic separation mechanisms
Elution modes: isocratic versus gradient
Batch chromatography
Continuous chromatography
Supercritical fluid chromatography
Solvent Recycling
Examples of Process Chromatography
Early process development
Implementation of SMB technology for chiral resolution
Global process optimization: combining synthesis and impurity removal
Chromatography versus crystallization to remove a genotoxic impurity
SMB mining - recover product from waste stream
Conclusions
References
Green Drug-Delivery Formulations
Introduction and Summary
Application of Green Chemistry in the Pharmaceutical Industry
Need for Green Chemistry Technologies to Deliver Low-Solubility Drugs
The need
Characteristics of low-solubility drugs
Low bioavailability
SDD Drug-Delivery Platform
Technology overview
Polymer choice
Process description
Formulation description
Dissolved drug
Drug in colloids and micelles
SDD efficacy
In Vitro testing
In Vivo testing
Green Chemistry Advantages of SDD Drug-Delivery Platform
Modeling
Reduction in waste due to efficient screening
Reduction of waste during manufacturing
Reduction in waste due to nonprogression of candidates
Reduction in waste due to lower dose requirements
Reduction in amount of drug that enters the environment
Calculated impact on waste reduction
Conclusions
Acknowledgments
References
Green Process Chemistry in the Pharmaceutical Industry: Recent Case Studies
Introduction
Sitagliptin: From Green to Greener; from a Catalytic Reaction to a Metal-Free Enzymatic Process
Saxagliptin: Elimination of Toxic Chemicals and the Use of a Biocatalytic Approach
Armodafinil: From Classical Resolution to Catalytic Asymmetric Oxidation to Maximize the Output
Emend: Elimination of the Use of Tebbe Reagent for Pollution Prevention and Utilization of Catalytic Asymmetric Transfer Hydrogenation
Greening a Process via One-pot or Telescoped Processing
Greening a Process via Salt Formation
Metal-free Organocatalysis: Applications of Chiral Phase-transfer Catalysis
Conclusions
References
Green Analytical Chemistry
Introduction
Method Assessment
Solvents and Additives for pH Adjustment
Sample Preparation
Techniques and Methods
Screening methods
Liquid chromatography
Gas chromatography
Supercritical fluid chromatography
Chiral analysis
Process analytical technology
Conclusions
Acknowledgments
References
Green Chemistry for Tropical Disease
Introduction
Interventions in Drug Dosing
Dose reduction through innovative drug formulation
Dose optimization: green dose setting
Active Pharmaceutical Ingredient Cost Reduction with Green Chemistry
Revision of the original manufacturing process
Case studies: manufacture of drugs for AntiRetroviral therapy
Case studies: Artemisinin combination therapies for malaria treatment
Conclusions
References
Green Engineering in the Pharmaceutical Industry
Introduction
Green Engineering Principles
Optimizing the use of resources
Life cycle thinking
Minimizing environment, health and safety hazards by design
More Challenge Areas for Sustainability in the Pharmaceutical Industry
Future Outlook and Challenges
References
Index

Edition: 2012
Publisher: John Wiley & Sons, Limited
Binding: Trade Cloth
Pages: 768
Size: 7.75" wide x 10.25" long x 1.75" tall
Weight: 3.19 lbs.
Language: English

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