title: 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.
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.
authors.affiliation: Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia. aelfaham@ksu.edu.sa.
authors.forename: Ayman
authors.initials: A
authors.lastname: El-Faham
authors.forename: Zainab
authors.initials: Z
authors.lastname: Al Marhoon
authors.forename: Ahmed
authors.initials: A
authors.lastname: Abdel-Megeed
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003606:Dacarbazine / Q000737:chemistry*; D004952:Esters; D010091:Oximes / Q000737:chemistry*
chemical_list: D000085:Acetates; D000596:Amino Acids; D004952:Esters; D010091:Oximes; C548311:ethyl 2-cyano-2-(hydroxyimino)acetate; D003606:Dacarbazine