Application of Modern Tools in Organic Synthesis
Biotage Summer Program held at the University of Richmond
Speaker’s Presentation Agenda
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《 DAY 1 》
#1: Expanding the scope of microwave-promoted organic synthesis
Nicholas Leadbeater, University of Connecticut
Microwave irradiation is fast becoming the heating method of choice for many organic transformations. However there are issues when it comes to scale-up of reactions and reaction monitoring as well as needs for expanding the scope of the technology. In this presentation, we will show how we have addressed the need for scale to at least the multi-gram and will focus particularly on batch processing. We will show how we have addressed issues of reaction monitoring by using in-situ Raman spectroscopy. In addition, we will present some of our recent methodology developments, particularly those focused around cleaner, greener approaches to key metal-catalyzed tranformations and reactions involving gaseous reagents.
#2: Application of Novel Synthetic Tools In Medicinal Chemistry
Ping Cao, GlaxoSmithKline
An array of novel synthetic tools emerged in recent years and they greatly enhanced the landscape of the chemical synthesis. Microwave assisted chemical methods are proven a powerful technique for increasing the throughput of chemical synthesis. Immobilized reagents on solid support are highly attractive in view of their well-known attributes for handling and purification. In this talk, we will present examples, which highlight the flexibility a medicinal chemist can take to apply these novel tools to facilitate the organic synthesis.
#3: Integrating Microwave Synthesis with Emerging Chemical Technologies
Bruce Clapham, Abbott ・・・ Day 1_#3_abbott.pdf(996.7KB)
This talk describes the integration of microwave chemistry within a high-throughput organic synthesis laboratory. The development of an automated monomer storage facility, a desktop library design LIMS tool and introduction of automated flow-hydrogenation and V-10 evaporation systems will be discussed. |
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《 DAY 2 》
#1: Nitrile anion acylation to form beta-ketonitriles as useful templates for hetelocycle synthesis.
William Trenkle, NIDDK, NIH
Research in our group has uncovered a facile method for the direct synthesis of beta- ketonitriles from unactivated esters. The resultant beta-ketonitriles are useful as a number of heterocycles via the corresponding beta-enamino- nitrile. Despite the utility of beta-enamino- nitriles in the synthesis of heterocyclic structures, there is a lack of general method for the synthesis of differentially substituted enamino-nitriles. Utilization of beta-ketonitriles as a template for unnatural 5- and 6-substituted cytosine derivatives and piperidine structures will also be described.
#2: Microwave-Assisted Synthesis Utilizing Supported Reagents: Rapid & Versatile Synthesis of Pharmaceutically Relevant Molecules
Paul Humphries, Pfizer ・・・ Day 2_#2_Pfizer.pdf(164.4KB)
The application of microwave heating to a polymer-/silica-assisted solution-phase synthesis technique has been utilized:- (i) a rapid and efficient two-step protocol for the preparation of pyrazoles from aryl methyl ketone and aryl hydrazine monomers has been developed, (ii) evaluation of the Pd EnCatTM family of catalysts in microwave-assisted Suzuki, Heck, and Sonogashira reactions, and (iii) silica-bound cyanoborohydride and carbodiimide: efficient alternatives for microwave-assisted reductive aminations and amide bond formations.
#3: Scaling-up Microwave Assisted Organic Reactions in the Advancer Kilobatch.
Joseph Pawluczyk, Merck ・・・ Day2 #3_Merck.pdf(695.3KB)
Microwave technology has increasingly become a valuable tool for the synthetic chemist. Microwave technology has opened the door to faster reaction times, higher yielding reactions and success in some cases where conventional conditions failed. Despite these advances, synthesizing large quantities of material remains problematic due to the scaling limitations of bench top microwave instruments. This talk will present some of our work with the Advancer in preparing multi-gram quantities of synthetic intermediates. |
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《 DAY 3 》
#1: The Application of Microwave Acceleration to the Synthesis of Pyrrole Containing Marine Natural Products
John Gupton, University of Richmond ・・・ Day 3_#1_DrGupton.pdf(5,918.9KB)
For some time now our research group has been interested in using vinylogous iminium salts as key building blocks in heterocyclic synthesis. More recently we have found that key transformations involving condensation reactions of vinamidinium salts with glycinate esters to forms pyrroles can be microwave accelerated. In addition, we have also explored microwave acceleration of Vilsmeier-Haack formylations, aminocarbonylations and Suzuki cross-coupling reactions of pyrrole intermediates, which subsequently served as key synthetic methods for the construction of several marine natural products. Ongoing work in this area will be presented.
#2: The use and application of solid supported reagents in organic, medicinal and scale up chemistries – leaping hurdles
Nathalie Huther, Biotage ・・・ Day 3_#2_Biotage.pdf(1,817.3KB)
The use of supported reagents and scavengers has become commonplace in a number of applications and processes. This talk will highlight key transformations, illustrating fundamentals and advantages over traditional techniques of the use of the solid supported media in a variety of different chemistries. |
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