Open AccessAmino acid sulfonamides based on 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride
Author(s) -
Anastasiia Riabchenko,
O. V. Shablykina,
S. V. Shilin,
С. А. Чумаченко,
V. P. Khilya
Publication year - 2020
Publication title -
ukrainica bioorganica acta
Language(s) - English
Resource type - Journals
eISSN - 1814-9766
pISSN - 1814-9758
DOI - 10.15407/bioorganica2020.02.027
Subject(s) - chemistry , sulfonyl , sulfonamide , triethylamine , benzoic acid , aqueous solution , chloride , hydrolysis , medicinal chemistry , organic chemistry , isocoumarin , alkyl
The creation of new amino acid derivatives of 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride 1 was investigated. The interaction of the sulfonyl chloride 1 with amino acid methyl esters (hydrochlorides) in 1,4-dioxane in the presence of triethylamine led to the corresponding amino acid sulfonamide derivatives of isocoumarin. The reaction of the sulfonyl chloride 1 with phenylalanine in the basic aqueous solution was complicated by the lactone system disclosure and led to 2'-carboxydeoxybenzoin ultimately (namely, 2-(2-(4-(N-(1-carboxy-2-phenylethyl)sulfamoyl)phenyl)-2-oxoethyl)benzoic acid). Similar product was obtained by the alkali hydrolysis of methyl ((4-(1-oxo-1H-isochromen-3-yl)phenyl)sulfonyl)leucinate.