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

Felikss Mutulis 1 , Máté Erdélyi 2,3,* email, Ilze Mutule 1 , Jana Kreicberga 1,4 email, Sviatlana Yahorava 1 , Aleh Yahorau 1 , Larisa Borisova-Jan 5 email and Jarl E.S. Wikberg 1,* email
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; in revised form: 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

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Cite This Article

MDPI and ACS Style

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.

AMA Style

Mutulis F, Erdélyi M, Mutule I, Kreicberga J, Yahorava S, Yahorau A, Borisova-Jan L, Wikberg JE. 2-(p-Hydroxybenzyl)indoles - Side Products Formed Upon Cleavage of Indole Derivatives from Carboxylated Wang Polymer - an NMR Study. Molecules. 2003; 8(10):728-734.

Chicago/Turabian Style

Mutulis, Felikss; Erdélyi, Máté; Mutule, Ilze; Kreicberga, Jana; Yahorava, Sviatlana; Yahorau, Aleh; Borisova-Jan, Larisa; Wikberg, Jarl E. 2003. "2-(p-Hydroxybenzyl)indoles - Side Products Formed Upon Cleavage of Indole Derivatives from Carboxylated Wang Polymer - an NMR Study." Molecules 8, no. 10: 728-734.

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