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Molecules 2003, 8(10), 728-734; https://doi.org/10.3390/81000728

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

1
Department of Pharmaceutical Biosciences, Division of Pharmaceutical Pharmacology, Uppsala Biomedical Center, Uppsala University, SE-751 24 Uppsala, Sweden
2
Department of Medicinal Chemistry, Division of Organic Pharmaceutical Chemistry, Uppsala Biomedical Center, Uppsala University, SE-751 24 Uppsala, Sweden
3
Department of Organic Chemistry, Uppsala University, Box 531, SE-751 21, Uppsala, Sweden
4
Faculty of Material Science and Applied Chemistry, Riga Technical University, Azenes 14/24, LV- 1048, Riga, Latvia
5
Melacure Therapeutics AB, Ulleråkersvägen 38, SE-756 43 Uppsala, Sweden
*
Authors to whom correspondence should be addressed.
Received: 19 December 2002 / Revised: 19 August 2003 / Accepted: 20 August 2003 / Published: 31 October 2003
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Abstract

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 %). View Full-Text
Keywords: Carboxylated Wang polymer; side reaction; p-hydroxybenzylation; 1; 2-ethanedithiol; NMR Carboxylated Wang polymer; side reaction; p-hydroxybenzylation; 1; 2-ethanedithiol; NMR
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Mutulis, F.; Erdélyi, M.; Mutule, I.; Kreicberga, J.; Yahorava, S.; Yahorau, A.; Borisova-Jan, L.; Wikberg, J.E. 2-(p-Hydroxybenzyl)indoles - Side Products Formed Upon Cleavage of Indole Derivatives from Carboxylated Wang Polymer - an NMR Study. Molecules 2003, 8, 728-734.

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