C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
C07C 229/22 (2006.01) C07C 227/32 (2006.01) C07C 239/18 (2006.01) C07D 307/66 (2006.01)
Patent
CA 2507669
The invention concerns a method for preparing 4-hydroxyisoleucine diastereoisomers and enantiomers and derivatives thereof of general formula (I), characterized in that it consists in reducing an isoxazole derivative of formula (II) in conditions directly resulting in the derivatives of formula (I), or in obtaining at least a lactone of structure (III) in racemic form(s), or a enantiomerically enriched mixture, followed by opening, in basic conditions, in an aprotic or protic solvent, the desired lactone(s) and, optionally, separating the desired form. The invention is useful for preparing in particular (2S, 3R, 4S)-4-hydroxyisoleucine.
L'invention a pour objet un procédé de préparation de diastéréoisomères et d'énantiomères de la 4-hydroxyisoleucine et de ses dérivés de formule générale (I) caractérisé en ce qu'il comprend la réduction d'un dérivé d'isoxazole de formule (II) dans des conditions conduisant directement aux dérivés de formule (I), ou à l'obtention d'au moins une lactone de structure (III) sous forme(s) racémique(s), ou d'un mélange énantiomériquement enrichi, suivie de l'ouverture, en conditions basiques, dans un solvant aprotique ou protique, de la lactone ou des lactones recherchées et, si nécessaire, de la séparation de la forme recherchée. Application à la préparation, en particulier, de la (2S, 3R, 4S)-4-hydroxyisoleucine.
Becht Jean-Michel
Catala Cedric
de Lamo Marin Sandra
Mioskowski Charles
Wagner Alain
Bereskin & Parr Llp/s.e.n.c.r.l.,s.r.l.
Centre National de La Recherche Scientifique (c.n.r.s.)
Universite Louis Pasteur
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