C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
C07C 227/16 (2006.01) C07B 55/00 (2006.01) C07B 57/00 (2006.01) C07C 227/30 (2006.01)
Patent
CA 2524489
The invention relates to a method for the synthesis of two isomers, at function OH, alone or in mixtures, of amino acids .alpha. or the derivatives thereof, having general formula (B), wherein: linkage C-O of the 4-position carbon (represented by symbol ) denotes one or other of isomers III or IV, or mixtures thereof. Moreover, R¿1? and R¿2? represent: a hydrogen atom; or either R¿1? or R¿2? represents a hydrogen atom and the other substituent is a radical R¿a?, an acyl group -COR¿a?, such as acetyl, or a functional group -COOR¿a?, -SO¿2?R¿a?, -N (R¿a?, R¿b?), R¿a? and R¿b?, which are identical or different, representing a C1-C12 linear or branched alkyl radical, optionally substituted, an aryl group with one or more aromatic rings and heterocycles, comprising between 5 and 8C, optionally substituted, or aralkyl, the alkyl substituent and the aryl group being as defined above; or R¿1? and R¿2? both represent a substituent as defined above. R¿3 ?represents a hydrogen atom or R¿a? and R¿4? has the significance of R¿a?. The invention is characterised in that it comprises: the isomerisation of a compound having formula (I), wherein R¿1?, R¿2?, R¿a?, R¿3? and R¿4? are as defined above, such as to produce a compound having formula (II); and the reduction of the carbonyl function thereof which, depending on the catalytic system employed and the formula (I) compound used, produces one of the isomers having general formula (III) or (IV) or a mixture thereof having formula (B). The invention can be used for the synthesis of (2S, 3R, 4S)-4-hydroxyisoleucine.
L'invention a pour objet un procédé de synthèse des deux isomères , au niveau de la fonction OH, seuls ou en mélanges, des acides aminés .alpha., ou de leurs dérivés, de formule générale (B): selon la revendication 1.
Catala Cedric
Mioskowski Charles
Wagner Alain
Bereskin & Parr Llp/s.e.n.c.r.l.,s.r.l.
Centre National de La Recherche Scientifique (cnrs)
Universite Louis Pasteur
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