Artículo
One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals
Fecha de publicación:
01/2001
Editorial:
Elsevier Science
Revista:
Journal of Molecular Catalysis B: Enzymatic
ISSN:
1381-1177
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
A lipase-catalyzed procedure is described for the one-pot conversion of carboxylic acids into substituted amides via in-situ formation of the ethyl ester and subsequent aminolysis. The procedure was optimized for the preparation of tetrahydro-N-[3-(methylamino)-propyl]-2-furancarboxamide, an intermediate in the synthesis of Alfuzosin, a reducing agent of symptoms associated with benign prostatic hypertrophy. This methodology proved to be general and can be applied to open-chain, cyclic, hydroxy-, amino-, dicarboxylic, various chain lengths, and unsaturated acids. Moreover, the enzyme shows a regioselective behavior in relation to primary and secondary amino groups. The procedure involved the treatment of the corresponding carboxylic acid with ethyl alcohol in presence of immobilized Candida antarctica lipase followed by addition of amine. The amide is obtained in good yields and regioselective way.
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Articulos(UMYMFOR)
Articulos de UNID.MICROANAL.Y MET.FISICOS EN QUIM.ORG.(I)
Articulos de UNID.MICROANAL.Y MET.FISICOS EN QUIM.ORG.(I)
Citación
Baldessari, Alicia; Mangone, Constanza P.; One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 11; 4-6; 1-2001; 335-341
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