C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 305/14 (2006.01)
Patent
CA 2597174
The invention concerns a method for preparing paclitaxel characterized in that it consists in starting with 10-deacetylbaccatine in accordance with a "one-pot" reaction including the following three steps: a) protecting the hydroxy radical in position 7 of 10-deacetylbaccatine with a silylated radical, then b) acetylating the hydroxy radical in position 10, c) optionally crystallizing the resulting baccatine III derivative, followed by condensation of (4S,5R)-3-N-benzoyl-2RS-methoxy-4-phenyl-l,3- oxazolidine-5-carboxylic acid, by esterifying in position 13 the acetylated 10-baccatine III derivative previously obtained, then opening the oxazolidine of the cyclic side chain and simultaneously releasing the hydroxy radical in position 7.
Procédé de préparation du paclitaxel caractérisé en ce que l'on opère à partir de la 10-déacétylbaccatine selon une réaction « one-pot » impliquant les 3 étapes successives suivantes : a) protection du radical hydroxy en position -7 de la 10-DAB par un radical silylé, puis b) acétylation du radical hydroxy en position -10, c) éventuellement cristallisation du dérivé de baccatine III obtenu, suivies de la condensation de l'acide (4S,5R)-3-N-benzoyl-2RS-méthoxy- 4-phényl-l,3- oxazolidine-5-carboxylique, par estérifïcation en position -13 du dérivé 10-acétylé de baccatine III obtenu précédemment, puis ouverture de l'oxazolidine de la chaîne latérale cyclique et libération simultanée du radical hydroxy en position -7, de son radical protecteur et purification éventuelle du paclitaxel obtenu.
Perley-Robertson Hill & Mcdougall Llp
Seripharm
LandOfFree
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