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Journal of the Mexican Chemical Society
versión impresa ISSN 1870-249X
J. Mex. Chem. Soc vol.53 no.3 Ciudad de México jul./sep. 2009
Article
Preparation and supporting on solid phase of chiral auxiliary (S)4(4hydroxybenzyl)oxazolidin2one from Ltyrosinol assisted by Microwaves
Adriana Cruz1 and Ignacio A. Rivero1,2 *
1 Centro de Graduados e Investigación en Química, Instituto Tecnológico de Tijuana. C.P. 1166. Tijuana, B.C. 22000, México.
2 Instituto Nacional de Investigaciones Nucleares, Departamento de Química. Carretera México Toluca S/N, La Marquesa, Ocoyoacac, México, D.F. C.P. 52750. *Responsible author: irivero@tectijuana.mx.
Received June 4, 2009
Accepted August 11, 2009
Abstract
An oxazolidinone chiral auxiliary, (S)(4Hydroxybenzyl)1,3oxazolidin2one 4 was prepared in 2380 % yield from Ltyrosinol using different methodologies. In solution, compound 4 was protected with a benzyl group on the phenolic hydroxyl 5a, which allowed the optimization of the solid phase synthesis of 5b5d. Chiral auxiliaries 5a and 5b reacted in solution with an α, βunsaturated system to give (S)4(4(benzyloxy)benzyl)1,3oxazolidin2one 6a. By contrast, in solid phase the same reaction afforded 6b. Both reactions were carried out under microwave activation. New compounds were characterized by 1H and 13C NMR, infrared spectroscopy and mass spectrometry.
Keywords: Oxazolidinones, chiral auxiliaries, solid phase synthesis.
Resumen
En este trabajo se reporta la preparación del nuevo auxiliar quiral de tipo oxazolidinona, (S)(4hidroxibencil)1,3oxazolidin2ona 4 que fue preparado a partir del Ltirosinol utilizando diferentes metodologías, con rendimientos que fluctúan en un intervalo de 2380 %, dependiendo del método. El compuesto 4 fue preparado en solución, protegidos con el grupo benciloxi en el hidroxilo fenólico 5a, para llevar a cabo la optimización de la síntesis en fase sólida de 5b5d. Los auxiliares quirales 5a y 5b fueron adicionados en solución a un sistema α, βinsaturado, obteniéndose a la (S)4(4(benciloxi)bencil)1,3oxazolidin2ona 6, mientras que en fase sólida se observó la formación del compuesto 6b. Estas reacciones fueron activadas con microondas. Todos los compuestos fueron caracterizados mediante RMN (1H y 13C), IR y EM.
Palabras Claves: Oxazolidinonas, auxiliares quirales, síntesis en fase sólida.
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Acknowledgments
We gratefully acknowledge support for this project by Consejo Nacional de Ciencia y Tecnología, México (CONACyT, GRANT No. SEP20147835), Dirección General de Educación Tecnológica, México (DGEST) and Institute of Chemistry from National Autonomus University of México. Adriana Cruz thanks to CONACyT for a graduate fellowship.
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