Process for performing retro-aldol reaction

C - Chemistry – Metallurgy – 07 – K

Patent

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C07K 1/107 (2006.01) C07C 45/51 (2006.01) C07C 227/16 (2006.01) C07C 229/02 (2006.01) C07K 1/12 (2006.01) C07K 7/56 (2006.01) C07K 7/64 (2006.01) C07K 11/02 (2006.01)

Patent

CA 2205369

A process for removing .beta.-hydroxy groups from .beta.-hydroxy-containing compounds is disclosed. The process involves the use of a retro-aldol- promoting reagent selected from the group consisting of trimethylamine-N- oxide, triethylamine-N-oxide, trimethylamine-N-oxide hydrate, and trimethylamine-hydrate and requires dissolution of the substrate in an aprotic solvent and reaction under elevated temperatures. The process is broadly applicable to a variety of substrates including complex cyclic peptides, linear peptides, and non-peptides.

Procédé d'extraction de groupes .beta.-hydroxy de composés contenant des .beta.-hydroxy. Le procédé consiste à utiliser un réactif stimulant le rétro-aldol, choisi dans le groupe constitué de triméthylamine-N-oxyde, triéthylamine-N-oxyde, triméthylamine-N-oxyde-hydrate et triméthylamine-hydrate, et nécessite la dissolution du substrat dans un solvant aprotique ainsi qu'une réaction à des températures élevées. Le procédé est globalement applicable à divers substrats, y compris des peptides cycliques complexes, des peptides linéaires et des non-peptides.

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