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    Green Techniques for Organic Synthesis and Medicinal Chemistry

    ISBN-10: 0470711515
    ISBN-13: 9780470711514
    Author(s): Wei Zhang, Berkeley Cue
    Description: 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  More...
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    Publisher: John Wiley & Sons, Limited
    Binding: Hardcover
    Pages: 768
    Size: 7.75" wide x 10.25" long x 1.75" tall
    Weight: 3.190
    Language: English

    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.

    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

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