Abstract
A new and efficient synthesis of a beta-lactam that is an advanced precursor of inhibitors of thrombin and tryptase is reported. The reaction sequence is based on the use of an inexpensive enantiomerically pure starting material and is designed to allow access to both enantiomers of the target molecules by epimerization of a side-product obtained along the synthesis. An improved procedure for the epimerization step that takes advantage of the use of a polymer-supported and recyclable phase-transfer catalyst is described.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antithrombins / chemical synthesis*
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Antithrombins / chemistry
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Antithrombins / pharmacology
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Catalysis
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Combinatorial Chemistry Techniques*
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Drug Design
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Indicators and Reagents
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Models, Molecular
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Molecular Structure
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Serine Endopeptidases
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Serine Proteinase Inhibitors / chemical synthesis*
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Serine Proteinase Inhibitors / chemistry
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Serine Proteinase Inhibitors / pharmacology
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Stereoisomerism
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Tryptases
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beta-Lactams / chemical synthesis*
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beta-Lactams / chemistry
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beta-Lactams / pharmacology
Substances
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Antithrombins
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Indicators and Reagents
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Serine Proteinase Inhibitors
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beta-Lactams
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Serine Endopeptidases
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Tryptases