Abstract
In this work, an efficient microwave-assisted methodology for the esterification of unprotected α-amino acids is described. Ionic esterified amino acids were synthesized in satisfactory yields in a facile one-pot solventless protocol from unprotected amino acids and alcohols under acid catalysis (MsOH or p-TsOH) to afford the pure products after a simple work-up procedure. This procedure can also be extended to the preparation of long and short chain alkyl and benzyl esters.
Highlights
Microwave technology has become a powerful tool in organic synthesis which is able to grant access to a wide range of organic compounds in a very simple, swift and efficient way The use of microwave dielectric heating have been shown to dramatically reduce processing time and often leading to high purities and better yields to products as compared to conventional methods [1,2,3,4].Parallel synthesis of combinatorial libraries can be described as synthetic sequences using an ordered array of spatially separated reaction vessels under the same reaction conditions which generally yield a more or less extensive library of compounds [5]
Parallel synthesis has been reported under both conventional heating conditions and, more recently, under microwave irradiation for combinatorial chemistry [6]
We report a one-pot, solventless and highly versatile microwave-assisted methodology for the esterification and simultaneous salt formation of unprotected α-amino acids using long chain alcohols and simple organic acid catalysts [methanesulfonic acid (MsOH) and p-toluenesulfonic acid (p-TsOH)] to obtain ionic amino acids ester with organic anions
Summary
Microwave technology has become a powerful tool in organic synthesis which is able to grant access to a wide range of organic compounds in a very simple, swift and efficient way The use of microwave dielectric heating have been shown to dramatically reduce processing time and often leading to high purities and better yields to products as compared to conventional methods [1,2,3,4].Parallel synthesis of combinatorial libraries can be described as synthetic sequences using an ordered array of spatially separated reaction vessels under the same reaction conditions which generally yield a more or less extensive library of compounds [5]. Microwave technology has become a powerful tool in organic synthesis which is able to grant access to a wide range of organic compounds in a very simple, swift and efficient way The use of microwave dielectric heating have been shown to dramatically reduce processing time and often leading to high purities and better yields to products as compared to conventional methods [1,2,3,4]. Parallel synthesis has been reported under both conventional heating conditions and, more recently, under microwave irradiation for combinatorial chemistry [6]. In this regard, microwaves can allow a quick and simple optimization of reaction. Some of them show antisickling activity [10], protective properties against microorganism growth, as well as in the preservation of perishable food products [11]
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