One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals

Autores
Baldessari, Alicia; Mangone, Constanza P.
Año de publicación
2001
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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.
Fil: Baldessari, Alicia. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Mangone, Constanza P.. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Materia
ALFUZOSIN
LIPASE
ONE-POT SYNTHESIS
PHARMACEUTICAL INTERMEDIATES
SUBSTITUTED AMIDES
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/85158
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticalsBaldessari, AliciaMangone, Constanza P.ALFUZOSINLIPASEONE-POT SYNTHESISPHARMACEUTICAL INTERMEDIATESSUBSTITUTED AMIDEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A 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.Fil: Baldessari, Alicia. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Mangone, Constanza P.. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaElsevier Science2001-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/85158Baldessari, 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; 335-3411381-1177CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/s1381-1177(00)00018-7info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1381117700000187info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:30:03Zoai:ri.conicet.gov.ar:11336/85158instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:30:04.094CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals
title One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals
spellingShingle One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals
Baldessari, Alicia
ALFUZOSIN
LIPASE
ONE-POT SYNTHESIS
PHARMACEUTICAL INTERMEDIATES
SUBSTITUTED AMIDES
title_short One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals
title_full One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals
title_fullStr One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals
title_full_unstemmed One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals
title_sort One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals
dc.creator.none.fl_str_mv Baldessari, Alicia
Mangone, Constanza P.
author Baldessari, Alicia
author_facet Baldessari, Alicia
Mangone, Constanza P.
author_role author
author2 Mangone, Constanza P.
author2_role author
dc.subject.none.fl_str_mv ALFUZOSIN
LIPASE
ONE-POT SYNTHESIS
PHARMACEUTICAL INTERMEDIATES
SUBSTITUTED AMIDES
topic ALFUZOSIN
LIPASE
ONE-POT SYNTHESIS
PHARMACEUTICAL INTERMEDIATES
SUBSTITUTED AMIDES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv 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.
Fil: Baldessari, Alicia. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Mangone, Constanza P.. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
description 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.
publishDate 2001
dc.date.none.fl_str_mv 2001-01
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/85158
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
1381-1177
CONICET Digital
CONICET
url http://hdl.handle.net/11336/85158
identifier_str_mv 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
1381-1177
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/s1381-1177(00)00018-7
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1381117700000187
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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