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Preparative Enantioselective Chromatography

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ISBN-10: 1405118709

ISBN-13: 9781405118705

Edition: 2005

Authors: Geoffrey B. Cox

List price: $315.00
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Description:

Written for chemists, chemical engineers, and analytical chemists, Preparative Enantioselective Chromatography demonstrates the considerable value of preparative enantioselective liquid chromatography in contemporary discovery, development, and production scale chemistry. By briefly covering basic preparative chromatography and chiral stationary phases for preparative use, method development and practical applications, the first part of this book serves as an ideal introduction to the technology for laboratory and pilot plant scale application.
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Book details

List price: $315.00
Copyright year: 2005
Publisher: John Wiley & Sons, Incorporated
Publication date: 6/17/2005
Binding: Hardcover
Pages: 344
Size: 6.75" wide x 9.50" long x 1.25" tall
Weight: 1.980

Contributors
Preface
Chiral chromatography in support of pharmaceutical process research
Introduction
A brief introduction to chirality
Why chirality is important
Accessing enantiopurity: a brief overview of approaches
Enantiopure starting materials: the chiral pool
Removable enantioenriched auxiliaries
Enantioselective catalysis
Resolution technologies: introduction
Chromatographic productivity is the key metric for preparative chromatography
Stationary phases for preparative chiral chromatography
Advantages of preparative chiral chromatography over other approaches for accessing enantiopure materials
Simulated moving bed enantioseparation
Green enantioseparation
What is the appropriate role of preparative chromatography in organic synthesis?
Fording the river at the easiest point: some observations on the appropriate placement of a chromatographic resolution within a chiral synthesis
Origins of preparative chiral chromatography
Practical tips for preparative chromatographic enantioseparation
Conclusion
Introduction to preparative chromatography
Introduction
Adsorption isotherms
The simple case - the Langmuir isotherm
Other isotherms
Competitive isotherms
Kinetics
Metrics for preparative operations
Throughput
Production rate
Productivity
Specific productivity
Cost
The influence of chromatographic parameters on preparative chromatography
Effect of particle size on preparative performance
Effects of pressure
Effects of column efficiency
Effect of column length
The effects of selectivity
Economics of preparative separations
Point of insertion of the chromatographic resolution in the synthetic route
Chiral stationary phases for preparative enantioselective chromatography
Summary
Introduction
Historical development of CSPs for preparative chromatography
Preparative CSPs
Classification of CSPs
Polymeric phases
Brush-type CSPs
Chiral phases for ligand-exchange chromatography
Imprinted phases
Chemical and physical properties of CSPs
Loading capacity
Chemical and physical stability
Solubility of the chiral solute
New and future developments in the field of preparative CSPs
CSPs with improved loading capacity
CSPs with improved selectivity
Immobilised polysaccharide-based CSPs
Conclusion
Method development for preparative enantioselective chromatography
Introduction
Chiral stationary phases for enantioselective chromatography
Screening and optimisation strategy for preparative chiral chromatography
Choice of the stationary phase
Choice of the mobile phase
Screening and optimisation of specific phases
Additives in the mobile phase
Preparative separations, criteria and objectives
Loadability and productivity
Selectivity and productivity
Solubility and productivity
Viscosity and productivity
Chemical and enantiomeric stability
Scale-up issues
Laboratory-scale separations
Large-scale separations
Conclusion
Scaling-up of preparative chromatographic enantiomer separations
Introduction
Analytical screening models
Standard procedure
Fast analytical screening process
Scaling-up from milligram to kilogram quantities
Introduction
Separation of a xanthone derivative
Separation of 'dibenzocycloheptanol' derivative
Separation of a 'pyrido-pyrimidin-4-one' derivative
Separation of a piperazinyl-piperidine derivative
Summary - scale-up
Larger scale separations
Introduction
Separation of a 'pyrolidino-quinolinone' derivative
Scale-up problems in early development
Introduction
Separation of a 'tetracyclic' compound
Non-natural amino acids
Separation of an 'indole' derivative
Summary
General conclusions
Steady-state recycling and its use in chiral separations
Overview
Introduction
SSR - concept and operation
Concept
Operation
Role of the injection loop
Case studies
Case study 1
Case study 2
Case study 3: collection of three SSR fractions
Conclusions
Simulated moving bed and related techniques
Overview
The SMB concept
Modeling of SMB processes
Design of SMB processes
Simulation of SMB processes
Influence of the equilibrium adsorption isotherms
Influence of mass transfer resistance
SMB related techniques
Varicol processes
Pseudo-SMB processes
Preparative-scale supercritical fluid chromatography
Introduction
History of SFC at GlaxoSmithKline
Principles of SFC
Advantages of SFC
Drawbacks of preparative SFC
Use of SFC
Chiral separation using SFC
Achiral separation using SFC
Consideration of preparative SFC
Future direction and development
Conclusion
Equipment for preparative and large size enantioselective chromatography
Introduction
The heart of the chromatographic process: the column
Packing technique, bed formation and bed consolidation
The wall region
Heat dissipation
Column technology
Column design
Equipment considerations for batch chromatography
Recycling
Detection
Supercritical fluid chromatography
Principle
Technical aspects
Eluent
Pumping
Injection
Detection
Product recovery
Eluent recycling
High-pressure technology, safety aspects
Multicolumn continuous chromatographic processes
Simulated moving bed
VARICOL
Case study in production-scale multicolumn continuous chromatography
Introduction
Chromatographic process research
Introduction
Selection of racemate to separate
Choice of the chromatographic conditions
Choice of the separation technique
Process development
Optimisation of the chemical steps
Production facts
Introduction
Implementation in a cGMP production environment
Qualification
Validation
Production and maintenance data
Further areas of development
Contract manufacturing and outsourcing considerations
Introduction
The regulatory agencies and the chiral market
Contract manufacturing
Time constraints
Risk of capital investment
Expertise
Intellectual property
Location
Primary or secondary supplier
Selecting the outsourcing partner
Expectations
Audit
Decision grid
Communication
Contact matrix
Frequent updates
Project requirements
R&D - method development
Clinical trial quantities
Trial runs vs production runs
Commercial-scale quantities
Schedule
Quantity
Product quality
Transfer of information
Feed characterization
Separation conditions
The chiral stationary phase
Analytical methods
Impurity specifications
Final product
Other considerations
End of the project
Economics
Productivity
Production rate
Cost breakdown
Clinical trial quantities
Commercial-scale quantities
Conclusion
Advanced concepts
Index