Process for producing erythromycin derivatives

Details Process for producing erythromycin derivatives Process for producing erythromycin derivatives

C - Chemistry, Metallurgy

07

H

C07H 17/08 (2006.01)

Patent

CA 2228254

The hydroxyl group in position 2' of erythromycin A is acetylated, the hydroxyl group in position 4" is formylated and subjected to reaction for the formation of hemiketal; subsequently, the hydroxyl group in position 11 is oxidized and the hydroxyl group in position 12 is alkylated, followed by removal of the acetyl group in position 2' and the formyl group in position 4" to yield a compound; the compound is reacted with benzyloxycarbonyl chloride under basic conditions and, thereafter, the introduced benzyloxycarbonyl group is removed and the nitrogen atom in position 3' is subsequently alkylated, followed by conversion to a fumarate in a crude crystal form, which is then recrystallized from an alcoholic solvent, followed by another recrystallization with hydrous ethyl acetate to produce a fumarate of the general formula (II): Image (where R1 is a lower alkyl group and R2 is a lower alkyl group). -45-

Procédé d'élaboration de sels d'acide fumarique appartenant à des composés de la formule générale (II). Dans cette formule, R1 et R2 sont des alkyles inférieurs. Ce procédé se caractérise par les étapes consistant à faire réagir un composé qui est élaboré à partir de l'érythromicine A en procédant à l'acétylation de l'hydroxyle en position 2', la formulation et l'hémicétalisation de l'hydroxyle en position 4", l'oxydation de l'hydroxyle en position 11, l'alkylation de l'hydroxyle en position 12 et l'extraction de l'acétyle en position 2' et du formyle en position 4", avec le chlorure de benzyloxycarbonyle en conditions basiques. Le composé obtenu est libéré du groupe benzyloxycarbonyle ainsi introduit; l'atome d'azote est alkylé en position 3', le composé obtenu est converti en un sel d'acide fumarique; le sel brut obtenu est recristallisé à partir d'un solvant alcoolique et le cristal obtenu est recristallisé à partir de l'acétate d'éthyle hydraté.

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