One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals
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 interme...
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2001
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v11_n4-6_p335_Baldessari http://hdl.handle.net/20.500.12110/paper_13811177_v11_n4-6_p335_Baldessari |
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paper:paper_13811177_v11_n4-6_p335_Baldessari2023-06-08T16:12:18Z One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals Baldessari, Alicia Mangone, Constanza Pía 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 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. Fil:Baldessari, A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Mangone, C.P. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2001 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v11_n4-6_p335_Baldessari http://hdl.handle.net/20.500.12110/paper_13811177_v11_n4-6_p335_Baldessari |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 Baldessari, Alicia Mangone, Constanza Pía One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals |
| topic_facet |
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 |
| 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. Copyright © 2001 Elsevier Science B.V. |
| author |
Baldessari, Alicia Mangone, Constanza Pía |
| author_facet |
Baldessari, Alicia Mangone, Constanza Pía |
| author_sort |
Baldessari, Alicia |
| title |
One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals |
| 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 |
| publishDate |
2001 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v11_n4-6_p335_Baldessari http://hdl.handle.net/20.500.12110/paper_13811177_v11_n4-6_p335_Baldessari |
| work_keys_str_mv |
AT baldessarialicia onepotbiocatalyzedpreparationofsubstitutedamidesasintermediatesofpharmaceuticals AT mangoneconstanzapia onepotbiocatalyzedpreparationofsubstitutedamidesasintermediatesofpharmaceuticals |
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