Side reactions in the preparation of 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
Autor: | Patricia Verheyden, Koen Iterbeke, Georges Laus, Dirk Tourwé |
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Rok vydání: | 1998 |
Předmět: | |
Zdroj: | Letters in Peptide Science. 5:121-123 |
ISSN: | 1573-496X 0929-5666 |
Popis: | During a study on the preparation of the conformationally restricted analogue of tryptophan into 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 1 by a Pictet–Spengler condensation with formaldehyde, two side products were detected: N-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 2 and a dimer 3 of two 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid units linked by a methylene group. Their structures were determined by HPLC-MS and 2D NMR spectroscopy. By changing the isolation procedure, the N-hydroxymethyl compound was removed. Treatment of the mixture with TFA in water converted the dimer into 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 1. |
Databáze: | OpenAIRE |
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