Enzymatic resolution of (RS)-2-(1-aminoethyl)-3-chloro-5-(substituted)pyridines
| Autor: | Amy E. Sigmund, Robert DiCosimo |
|---|---|
| Rok vydání: | 2004 |
| Předmět: |
chemistry.chemical_classification
Methyl propionate Resolution (mass spectrometry) Stereochemistry organic chemicals Organic Chemistry Ethyl acetate Substrate (chemistry) Catalysis Inorganic Chemistry chemistry.chemical_compound Enzyme chemistry Acetylation Pyridine heterocyclic compounds Physical and Theoretical Chemistry Enantiomeric excess circulatory and respiratory physiology |
| Zdroj: | Tetrahedron: Asymmetry. 15:2797-2799 |
| ISSN: | 0957-4166 |
| DOI: | 10.1016/j.tetasy.2004.07.043 |
| Popis: | The enantioselectivity of the lipase-catalyzed acetylation of several ( RS )-2-(1-aminoethyl)-3-chloro-5-(substituted)pyridines has been examined. An enantiomeric excess (substrate) of 94% at 55% conversion was obtained for acetylation of the ( R )-isomer of ( RS )-2-(1-aminoethyl)-3-chloro-5-bromopyridine by Candida antartica lipase B in ethyl acetate, whereas the ( R )-isomer of ( RS )-2-(1-aminoethyl)-3,5-dichloropyridine and ( RS )-2-(1-aminoethyl)-3-chloro-5-(difluoromethoxy)pyridine were each acetylated with significantly lower enantioselectivity. Substitution of methyl propionate, methyl isobutyrate or methyl methoxyacetate for ethyl acetate resulted in decreased enantioselectivity. |
| Databáze: | OpenAIRE |
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