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

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

1, 2,3,* , 1, 1,4
,
1, 1, 5
 and
1,*
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 %).
Keywords: Carboxylated Wang polymer; side reaction; p-hydroxybenzylation; 1; 2-ethanedithiol; NMR Carboxylated Wang polymer; side reaction; p-hydroxybenzylation; 1; 2-ethanedithiol; NMR
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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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