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Molecules 2013, 18(12), 14747-14759; doi:10.3390/molecules181214747
Article

OxymaPure/DIC: An Efficient Reagent for the Synthesis of a Novel Series of 4-[2-(2-Acetylaminophenyl)-2-oxo-acetylamino] Benzoyl Amino Acid Ester Derivatives

1,2,* , 1
,
3,4
 and
5,6,7,8,*
1 Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia 2 Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 12321, Egypt 3 Department of Botany and Microbiology, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia 4 Department of Plant Protection, Faculty of Agriculture, Saba Basha, Alexandria University, Alexandria 12321, Egypt 5 Institute for Research in Biomedicine (IRB), Barcelona Science Park, Baldiri Reixac 10, Barcelona 08028, Spain 6 CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Baldiri Reixac 10-12, Barcelona 08028, Spain 7 Department of Organic Chemistry, University of Barcelona, Martí i Franqués 1-11, Barcelona 08028, Spain 8 School of Chemistry & Physics, University of KwaZulu-Natal, Durban 4001, South Africa
* Authors to whom correspondence should be addressed.
Received: 24 September 2013 / Revised: 15 November 2013 / Accepted: 20 November 2013 / Published: 28 November 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

OxymaPure (ethyl 2-cyano-2-(hydroxyimino)acetate) was tested as an additive for use in the carbodiimide (DIC) approach for the synthesis of a novel series of α-ketoamide derivatives (4-[2-(2-acetylaminophenyl)-2-oxo-acetylamino]benzoyl amino acid ester derivatives). OxymaPure showed clear superiority to HOBt/DIC or carbodiimide alone in terms of purity and yield. The title compounds were synthesized via the ring opening of N-acylisatin. First, N-acetylisatin was reacted with 4-aminobenzoic acid under conventional heating as well as microwave irradiation to afford 4-(2-(2-acetamidophenyl)-2-oxoacetamido)benzoic acid. This α-ketoamide was coupled to different amino acid esters using OxymaPure/DIC as a coupling reagent to afford 4-[2-(2-acetylaminophenyl)-2-oxo-acetylamino]benzoyl amino acid ester derivatives in excellent yield and purity. The synthesized compounds were characterized using FT-IR, NMR, and elemental analysis.
Keywords: N-acetylisatin; 4-aminobenzoic acid; amino acid esters; DIC; OxymaPure; α-ketoamide N-acetylisatin; 4-aminobenzoic acid; amino acid esters; DIC; OxymaPure; α-ketoamide
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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El-Faham, A.; Al Marhoon, Z.; Abdel-Megeed, A.; Albericio, F. OxymaPure/DIC: An Efficient Reagent for the Synthesis of a Novel Series of 4-[2-(2-Acetylaminophenyl)-2-oxo-acetylamino] Benzoyl Amino Acid Ester Derivatives. Molecules 2013, 18, 14747-14759.

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