A process for the preparation of 3-glutamido bile ester...

C - Chemistry – Metallurgy – 07 – J

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C07J 75/00 (2006.01) C07J 41/00 (2006.01)

Patent

CA 2435010

The present invention relates to a novel process for the preparation of bile esters derivatives of general formula (I), in which R0 is H or OH; R1 is H, .alpha.-OH or .beta.-OH; R2 and R3 are independently hydrogen, straight or branched (C1-C20) alkyl optionally substituted with aryl; R5 is a straight or branched (C1-C4) alkyl and R6 is a straight or branched (C1-C4) alkyl or a benzyl group, via transamidation of the amine (V) with the 5-ocoproline derivative (II), wherein R4 is selected from the group consisting of tertbutoxycarbonyl, methoxycarbonyl, ethoxycarbonyl, 2- trimethylsilylethoxycarbonyl, cyclobutoxycarbonyl and 1-methylcyclobutoxy carbonyl, followed by the selective cleavage of the protecting group R4 under acidic conditions.

L'invention concerne un nouveau procédé de préparation de dérivés d'esters de bile de formule générale (I), dans laquelle R0 représente H ou OH, R1 représente H, .alpha.-OH ou .beta.-OH, R2 et R3 représentent indépendamment hydrogène, alkyl(C1-C20) linéaire ou ramifié éventuellement substitué avec un aryle, R5 représente alkyl(C1-C4) linéaire ou ramifié et R6 représente alkyl(C1-C4) linéaire ou ramifié ou un groupe benzyle, via une transamidation de l'amine (V) avec le dérivé (II) de 5-oxoproline, R4 étant sélectionné dans le groupe constitué par tertbutoxycarbonyle, méthoxycarbonyle, éthoxycarbonyle, 2-triméthylsilyléthoxycarbonyle, cyclobutoxycarbonyle et 1-méthylcyclobutoxy carbonyle, suivie d'un clivage sélectif du groupe protecteur R4 dans des conditions acides.

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