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- Title
Carbon‐13 synthesis and NMR spectroscopic geometric isomer evaluation to support the filing of teriflunomide.
- Authors
Kurz, Michael; Gretzke, Dirk; Hörlein, Rolf; Turpault, Sandrine; Atzrodt, Jens; Derdau, Volker
- Abstract
The two isotopomers of teriflunomide were synthesized starting from isotopically stable‐labeled stocks of [13C]potassium cyanide and [1‐13C]ethyl bromoacetate. The two 13C‐labeled compounds 1a, b were applied in several NMR studies to study the E/Z ratio in different matrices. In a solution, such as dimethyl sulfoxide (DMSO), a dynamic equilibrium between E/Z‐isomers (ratio of 8:92) was determined by initial 13C‐carbon NMR experiments. To get insights into the E/Z ratio of teriflunomide under in vivo conditions, advanced heteronuclear NMR (heteronuclear Overhauser effect spectroscopy [HOESY]) in D2O and mixtures of D2O/plasma were performed. Whereas NMR experiments in mixtures of water and plasma failed owing to extreme line broadening, NMR spectra in water at pH 7.4 showed only the Z‐isomer.
- Subjects
POTASSIUM cyanide; DIMETHYL sulfoxide; ISOMERISM; MIXTURES
- Publication
Journal of Labelled Compounds & Radiopharmaceuticals, 2021, Vol 64, Issue 2, p82
- ISSN
0362-4803
- Publication type
Article
- DOI
10.1002/jlcr.3876