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Abstract:

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. Copyright © 2001 Elsevier Science B.V.

Registro:

Documento: Artículo
Título:One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals
Autor:Baldessari, A.; Mangone, C.P.
Filiación:Departamento De Química Orgánica, Facultad De Ciencias Exactas Y Naturales, Universidad De Buenos Aires, Pabellón 2, Piso 3, 1428, Buenos Aires, Argentina
Palabras clave:Alfuzosin; Lipase; One-pot synthesis; Pharmaceutical intermediates; Substituted amides; alfuzosin; amide; triacylglycerol lipase; biocatalyst; Candida antarctica; conference paper; drug synthesis; enzyme immobilization; enzyme specificity; esterification; in vitro study; methodology; reaction analysis; technique
Año:2001
Volumen:11
Número:4-6
Página de inicio:335
Página de fin:341
DOI: http://dx.doi.org/10.1016/S1381-1177(00)00018-7
Título revista:Journal of Molecular Catalysis - B Enzymatic
Título revista abreviado:J. Mol. Catal. B Enzym.
ISSN:13811177
CODEN:JMCEF
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v11_n4-6_p335_Baldessari

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Citas:

---------- APA ----------
Baldessari, A. & Mangone, C.P. (2001) . One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals. Journal of Molecular Catalysis - B Enzymatic, 11(4-6), 335-341.
http://dx.doi.org/10.1016/S1381-1177(00)00018-7
---------- CHICAGO ----------
Baldessari, A., Mangone, C.P. "One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals" . Journal of Molecular Catalysis - B Enzymatic 11, no. 4-6 (2001) : 335-341.
http://dx.doi.org/10.1016/S1381-1177(00)00018-7
---------- MLA ----------
Baldessari, A., Mangone, C.P. "One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals" . Journal of Molecular Catalysis - B Enzymatic, vol. 11, no. 4-6, 2001, pp. 335-341.
http://dx.doi.org/10.1016/S1381-1177(00)00018-7
---------- VANCOUVER ----------
Baldessari, A., Mangone, C.P. One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals. J. Mol. Catal. B Enzym. 2001;11(4-6):335-341.
http://dx.doi.org/10.1016/S1381-1177(00)00018-7