dc.contributor.author | Zhao, Hua | en |
dc.contributor.author | Song, Zhiyan | en |
dc.contributor.author | Cowins, Janet V. | en |
dc.contributor.author | Olubajo, Olarongbe | en |
dc.date.accessioned | 2015-10-28T20:11:10Z | en |
dc.date.available | 2015-10-28T20:11:10Z | en |
dc.date.issued | 2008-01-16 | en |
dc.identifier.citation | Zhao, H., Song, Z., Cowins, J. V., & Olubajo, O. (2008). Microwave-Assisted Esterification of N-Acetyl-L-Phenylalanine Using Modified Mukaiyama’s Reagents: A New Approach Involving Ionic Liquids. International Journal of Molecular Sciences, 9(1), 33–44. MDPI AG. Retrieved from http://dx.doi.org/10.3390/ijms9010033 | en |
dc.identifier.issn | 1422-0067 | en |
dc.identifier.doi | 10.3390/ijms9010033 | en |
dc.identifier.uri | http://hdl.handle.net/11286/581395 | en |
dc.description.abstract | Inspired by the concept of ionic liquids (ILs), this study modified the original Mukaiyama’s reagent, 2-chloro-1-methylpyridinium iodide (m.p. 200-dec), from ionic solid into liquids by changing its anion. The esterification of N-acetyl-L-phenylalanine was investigated as a model reaction. The microwave irradiation was more effective in esterifying N-acetyl-L-phenylalanine than the conventional reflux method. The original Mukaiyama’s reagent was modified into ILs through manipulating its anion. However, only non-nucleophilic anions (such as EtSO4- and Tf2N-) were favorable since nucleophilic ones (such as CF3COO- and CH3COO-) could exchange with chlorine resulting in non-reactive coupling reagents. Two modified Mukaiyama’s compounds (i.e. hydrophilic [2- ClMePy][EtSO4] and hydrophobic [2-ClMePy][Tf2N]) have been identified as the best ILtype coupling reagents. The esterification reaction was greatly enhanced by using 1- methylimidazole as the base instead of conventional toxic tertiary amines, and by using excess amount of alcohols as solvents instead of dichloromethane. Overall, the method reported is effective and ‘greener’. | en |
dc.language.iso | en_US | en |
dc.publisher | MDPI | en |
dc.relation.url | http://www.mdpi.com/1422-0067/9/1/33 | en |
dc.subject | Savannah State University (Savannah, Ga.) | en |
dc.subject | Amino acid | en |
dc.subject | Ionic liquid | en |
dc.subject | Mukaiyama’s reagent | en |
dc.subject | Microwave | en |
dc.subject | Esterification | en |
dc.title | Microwave-Assisted Esterification of N-Acetyl-L-Phenylalanine Using Modified Mukaiyama’s Reagents: A New Approach Involving Ionic Liquids | en_US |
dc.type | Article | en |
dc.contributor.department | Savannah State University | en |
dc.identifier.journal | International Journal of Molecular Sciences | en |