Three-step conversion of protected taxane ester to paclitaxel

C - Chemistry – Metallurgy – 07 – D

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C07D 305/14 (2006.01)

Patent

CA 2445250

The present invention relates to a method of producing paclitaxel from a protected coupled ester compound having a formula: wherein P1 is a hydrogenatable protecting group, comprising deprotecting the 7-O-position and 3'-N-position of the protected coupled ester compound to form a first intermediate compound, benzoylating the first intermediate compound at the 31- N-position thereby to form a second intermediate compound, and deprotecting the second intermediate compound by replacing P1 with hydrogen in the presence of an acid. The present invention also provides chemical compounds useful in the production of paclitaxel.

La présente invention concerne un procédé de production de paclitaxel à partir d'un composé d'ester couplé protégé représenté par la formule dans laquelle P¿1? est un groupe de protection hydrogénable, consistant à déprotéger la position 7-O et la position 3'-N du composé d'ester couplé protégé pour former un premier composé intermédiaire, à procéder à la benzoylation du premier composé intermédiaire sur la position 3'-N- pour former ainsi un second composé intermédiaire, et à déprotéger le second composé intermédiaire par remplacement de P¿1? par de l'hydrogène en présence d'un acide. La présente invention concerne également des composés chimiques utilisés dans la production de paclitaxel.

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