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Int. J. Mol. Sci. 2008, 9(1), 33-44; doi:10.3390/ijms9010033

Microwave-Assisted Esterification of N-Acetyl-L-Phenylalanine Using Modified Mukaiyama’s Reagents: A New Approach Involving Ionic Liquids

Chemistry Program, Savannah State University, Savannah, GA 31404, USA
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Author to whom correspondence should be addressed.
Received: 30 November 2007 / Accepted: 10 January 2008 / Published: 16 January 2008
(This article belongs to the Special Issue Ionic Liquids)
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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’. View Full-Text
Keywords: amino acid; ionic liquid; Mukaiyama’s reagent; microwave; esterification. amino acid; ionic liquid; Mukaiyama’s reagent; microwave; esterification.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Zhao, H.; Song, Z.; Cowins, J.V.; Olubajo, O. Microwave-Assisted Esterification of N-Acetyl-L-Phenylalanine Using Modified Mukaiyama’s Reagents: A New Approach Involving Ionic Liquids. Int. J. Mol. Sci. 2008, 9, 33-44.

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