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

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
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 Chemistry)
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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. View Full-Text
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
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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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