SYNTHESIS PROCESS IN SYMMETRIC AND ASYMMETRIC BIS-PHOSPHORAMIDITE COMPOUNDS UNDER A MULTICOMPONENT REACTION

The present invention relates to a multicomponent reaction (MCR) for obtaining three bis-phosphoramidites, one asymmetric and two symmetric. Said reaction present in their structures nitrogen-phosphorus-oxygen (N-P=O) and nitrogen-phosphorus-sulfur (N-P=S) bonds, obtaining a library of six compounds...

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Hauptverfasser: RAMÍREZ SOTELO María Guadalupe, BAÑUELOS HERNÁNDEZ Angel Ernesto, CASTREJON FLORES José Luis, FRANCO PÉREZ José Marco Antonio, AGUILAR GUZMÁN Alma Josefina, ZAMUDIO MEDINA José Angel, PÉREZ HERNÁNDEZ Nury
Format: Patent
Sprache:eng ; spa
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Zusammenfassung:The present invention relates to a multicomponent reaction (MCR) for obtaining three bis-phosphoramidites, one asymmetric and two symmetric. Said reaction present in their structures nitrogen-phosphorus-oxygen (N-P=O) and nitrogen-phosphorus-sulfur (N-P=S) bonds, obtaining a library of six compounds by two MCR reactions (four symmetric and two asymmetric). In the first RCM using 1,2 diamino ethane, the following bis-phosphoramidites O,O,O',O'-tetraethyl ethane-1,2-diylbis(phosphoramidite) 5 with 23%, diphenyl (2-((diethoxyphosphorthiol) amino)ethyl)phosphoramidite 6 with 38% and tetraphenyl ethane-1,2-diylbis(phosphoramidite) 7 with 10%, with an overall yield of 71% of the three bis-phosphoramidites. In the second RCM using 1,3 diamino propane, the bis-phosphoramidites O,O,O',O'-tetraethyl propane-1,3-diylbis(phosphoramidite) 8 obtained with 14%, diphenyl (3-((diethoxyphosphorothiol)amino) propyl)phosphoramidite 9 with 25% and tetraphenyl propane-1,3-diylbis(phosphoramidite) 10 with 1 2%, with an overall yield of 51% of the three bis-phosphoramidites. The importance of said novel RCM lies in generating three bis-phosphoramidites in a single step by conventional synthesis, taking more than fifteen days to synthesize, purify and characterize them. Further, the present invention aims to save reaction time, solvents, reagents, purifications, catalysts, expensive equipment and reduce secondary products harmful to the environment. Finally, it is a sustainable process for synthesizing bis-phosphoramidites in a fast and simple way, friendly to the environment. Esta invención se basa en una reacción de multicomponentes (MCR), para la obtención de tres bisfosforamidatos uno asimétrico y dos simétricos. Los cuales presentan en sus estructuras enlaces nitrógeno-fósforo-oxigeno (N-P=O) y nitrógeno-fósforo-azufre (N-P=S). Obtuvimos una quimioteca de seis compuestos por dos reacciones de MCR, (cuatro simétricos y dos asimétricos). En la primera MCR utilizando la 1,2 diamino etano se obtuvieron los siguientes bisfosforamidatos O,O,O',O'-tetraetil etano-1,2-diilbis(fosforamidatioato) 5 con 23%, difenil (2-((dietoxifosforotiol)amino)etil)fosforamidato 6 con 38% y tetrafenil etano-1,2-diilbis (fosforamidato) 7 con 10%, con un rendimiento global del 71% de los tres bisfosforamidatos. En la segunda MCR utilizando 1,3 diamino propano se obtuvieron los bisfosforamidatos O,O,O',O'-tetraetil propano-1,3-diilbis(fosforam idatotioato) 8 con 14%, difenil (3-((dietoxifosforotiol)amino