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Synthesis of N-Dodecylethanamide-DTTA and characterization by mass spectrometry, NMR and IR spectroscopy

: Kongtso, Adeline
: Butenschön, Holger; Schuchardt, Sven

Hannover, 2012, V, 42 S.
Hannover, Univ., Bachelor Thesis, 2012
Bachelor Thesis
Fraunhofer ITEM ()
mass spectrometry; nuclear magnetic resonance spectroscopy; infrared spectroscopy

The objective of this thesis was the synthesis of N-dodecylethanamide-DTTA, a hydrophobic chelating agent for rare earth ions, by the method of activation with DCC/HOBt and by the imidazolide method. As starting material (Bis-(2-(bis-tbutoxycarbonylmethyl-amino)-ethyl)-amino)-acetic-acid-tbutoxycarbonylmethyl ester was used. Both methods were performed each over four steps: firstly, a selective splitting-off of a tbutoxycarbonyl group with formation of a carboxylic acid, following by activation of the carboxylic acid, then conversion of the carboxylic acid in an amide and finally splitting-off of remaining tbutoxycarbonyl groups. Despite the fact that the amide was obtained by both methods, the expected product, N-dodecylethanamide-DTTA, was not characterized in the organic layer after aqueous working up of the amide in the last step of the synthesis. In this work, Intermediates, products and byproducts were analyzed by MALDI/ESI-TOF mass spectrometry, NMR and IR spectroscopy.