TPTU applied in large scale applications for the synthesis of Pharmaceuticals, in particular in situations where sensitive functionality is present on the coupling partners, and as a consequence, mild reaction conditions are required.
Synonym: O-(2-Oxo-1(2H)pyridyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate
White to off-white crystalline
Store in a cool and dry place (2-8oC)
- TPTU together with HOBt have been used in coupling reactions, leading to the impressive outcomes of couplings free of racemization, thus are the reagents of choice for segment condensations.
- TPTU has been applied in the preparation of activated Fmoc-His(Trt)-OH, reducing the racemization. Application of these coupling methods improved the quality of the crude product significantly, thus, this contribution represents a further step towards an optimal strategy for the incorporation of His. This method helps to overcome the problem of racemization for the His residue, a prerequisite for the synthesis of large peptides and proteins.
- Coupling Methods for Fmoc-His(Trt)-OH Resulting in Minimal Racemization
M. Mergler, F. Dick, and Th. Vorherr BACHEM AG, Hauptstr., 144, CH-4416.
- Large-Scale Applications of Amide Coupling Reagents for the Synthesis of Pharmaceuticals
J. R. Dunetz, J. Magano, and G. A. Weisenburger Org. Process Res. Dev., 2016, 20, 140−177.