2-(p-Hydroxybenzyl)indoles - Side Products Formed Upon Cleavage of Indole Derivatives from Carboxylated Wang Polymer - an NMR Study

Molecules

Felikss Mutulis¹  Máté Erdélyi¹  Ilze Mutule¹  Jana Kreicberga¹  Sviatlana Yahorava¹  Aleh Yahorau¹  Larisa Borisova-Jan¹ 

[1] ¹Department of Pharmaceutical Biosciences, Division of Pharmaceutical Pharmacology, Uppsala Biomedical Center, Uppsala University, SE-751 24 Uppsala, Sweden

关键词: Carboxylated Wang polymer;    side reaction;    p-hydroxybenzylation;    1;    2-ethanedithiol;    NMR;   

DOI  :  10.3390/81000728

来源: mdpi

【 摘 要 】

Treatment of carboxylated Wang polymer attached to a 2-unsubstituted indole derivative with a trifluoroacetic acid based mixture resulted in a side reaction: p-hydroxybenzylation at the 2-position of the indole ring. The structure of the resulting N-3-aminopropyl)-N-benzyl-4-[2-(4-hydroxybenzyl)-1H-indol-3-yl]-butyramide trifluoroacetate was ascertained by a full assignment of its ¹H- and ¹³C-NMR spectra. The side reaction could be suppressed by the use of 1,2-ethanedithiol in high concentrations (16 %).

【 授权许可】

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