(Isocoumarin-3-yl)phenoxyacetic acids in the amino acid derivatives synthesis. Structure and activity

1Shilin, SV, 1Shablykina, OV, 1Ishchenko, VV, 1Khylia, VP
1Taras Shevchenko National University of Kyiv
Dopov. Nac. akad. nauk Ukr. 2017, 1:82-87
Section: Chemistry
Language: Ukrainian

The relative reactivities of (isocoumarin-3-yl)- and (3,4-dihydroisocoumarin-3-yl)phenoxyacetic acids in the synthesis of amino acid derivatives, which includes the activated N-hydroxysuccinimide esters producing, are studied. It is found that, for the compounds with unsaturated isocoumarin cycle, the rate of activated ester formation is significantly reduced, when a substituent (regardless of size) in the ortho position to the oxyacetic acid fragment appears. While the slowing interaction of their saturated analogues with N-hydroxysuccinimide is not observed due to the presence of the ortho substituent.

Keywords: (3, (isocoumarin-3-yl)phenoxyacetic acids, 4-dihydroisocoumarin-3-yl)phenoxyacetic acids, activated ester method, amino acid derivatives, N-hydroxysuccinimide

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