Aminolysis of ezetimibe
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F15%3A39899680" target="_blank" >RIV/00216275:25310/15:39899680 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1016/j.jpba.2015.01.019" target="_blank" >http://dx.doi.org/10.1016/j.jpba.2015.01.019</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.jpba.2015.01.019" target="_blank" >10.1016/j.jpba.2015.01.019</a>
Alternative languages
Result language
angličtina
Original language name
Aminolysis of ezetimibe
Original language description
The aminolysis of ezetimibe (1) and the structurally similar (3R*,4S*)-(4-fluoropheny1)-4-(4-hydroxyphenyl)-3-methylazetidin-2-one (4a) giving the corresponding beta-aminoamides 2a-d and 5a-c was studied spectrophotometrically under pseudo-first order conditions in aqueous butylamine, 3-methoxypropylamine, 2-methoxyethylamine and 2-hydroxyethylamine buffer solutions at 39 degrees C. It was found that the reaction mechanism involves uncatalyzed nucleophilic attack of an amine on the azetidinone carbonylgroup as the rate-limiting step. On the basis of the Bronsted beta(Nuc) value (0.58 and 0.55 respectively) an early transition state was proposed in which the extent of C-N-amine bond formation is low and the C-N-lactam bond remains almost intact. It wasalso found that the presence of the phenolic group has a crucial role in the aminolysis because the analogous O-methyl derivative 4b does not react with amines at all. This observation would explain the fact that aminolysis of ezetimibe
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
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Continuities
S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2015
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Pharmaceutical and Biomedical Analysis
ISSN
0731-7085
e-ISSN
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Volume of the periodical
107
Issue of the periodical within the volume
březen
Country of publishing house
GB - UNITED KINGDOM
Number of pages
6
Pages from-to
495-500
UT code for WoS article
000351116900066
EID of the result in the Scopus database
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