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Base-catalyzed rearrangement of Ezetimibe

Authors: Hanusek Jiří | Baťová Jana | Imramovský Aleš | Hájíček Josef

Year: 2011

Type of publication: ostatní - přednáška nebo poster

Page from-to: nestránkováno

Titles:

Language	Name	Abstract	Keywords
eng	Base-catalyzed rearrangement of Ezetimibe	We have focused on the determination of structure of product formed under base-catalyzed conditions in water (pH 8-14) and on the reaction mechanism of this reaction. We have found that Ezetimibe undergoes base-catalyzed rearrangement of β-lactam ring to tetrahydropyrane ring instead of expected hydrolysis of amide group. The kinetics and mechanism of this rearrangement have been studied in aqueous tertiary amine buffers at constant ionic strength and at 40 °C. It was found that the transformation is subject to specific base catalysis. The pH plot contains three regions. At pH 8–10 the log kobs increases linearly with pH (slope ≈ 1). At pH 10 there is a break downwards (slope ≈ 0) giving probably pKa of phenolic OH group (pKa ≈ 10) and at pH > 12 increases again as the new reaction pathway opens.	Ezetimibe, stability, rearrangement