(Isocoumarin-3-yl)phenoxyacetic acids in the amino acid derivatives synthesis. Structure and activity
DOI:
https://doi.org/10.15407/dopovidi2017.01.082Keywords:
(3, (isocoumarin-3-yl)phenoxyacetic acids, 4-dihydroisocoumarin-3-yl)phenoxyacetic acids, activated ester method, amino acid derivatives, N-hydroxysuccinimideAbstract
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.
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