Methods for manufacturing betulinic acid

Details Methods for manufacturing betulinic acid Methods for manufacturing betulinic acid

C - Chemistry, Metallurgy

07

C

C07C 69/013 (2006.01) C07C 45/64 (2006.01) C07C 47/46 (2006.01) C07C 51/16 (2006.01) C07C 51/367 (2006.01) C07C 62/32 (2006.01) C07C 67/03 (2006.01) C07C 67/08 (2006.01) C07C 67/29 (2006.01) C07C 67/39 (2006.01) C07C 69/00 (2006.01) C07C 69/732 (2006.01) C07J 63/00 (2006.01)

Patent

CA 2396574

The present invention provides a method for preparing betulin-3-acetate including alcoholyzing betulin 3,28-dibenzoate; a process for preparing betulin-3-acetate including: (1) acylating betulin to provide betulin 3,28- dibenzoate and (2) alcoholyzing betulin 3,28-dibenzoate to provide betulin-3- acetate; and a process for preparing betulinic acid including: (1) acylating betulin to provide betulin 3,28-dibenzoate; (2) alcoholyzing betulin 3,28- dibenzoate to provide betulin-3-acetate; (3) oxidizing betulin-3-acetate to provide betulinic aldehyde-3-acetate; (4) oxidizing betulinic aldehyde-3- acetate to provide betulinic acid-3-acetate; and (5) deprotecting betulinic acid-3-acetate to provide betulinic acid.

L'invention concerne un procédé de préparation de 3-acétate de bétuline, qui comporte une étape d'alcoolise de 3,28-dibenzoate de bétuline ; un procédé de préparation de 3-acétate de bétuline, qui comprend les étapes consistant à : (1) acyler de la bétuline pour obtenir du 3,28-dibenzoate de bétuline, et (2) alcooliser le 3,28-dibenzoate de bétuline pour obtenir du 3-acétate de bétuline ; et un procédé de préparation d'acide bétulinique qui comprend les étapes consistant à : (1) acyler la bétuline pour obtenir du 3,28-dibenzoate de bétuline, (2) alcooliser le 3,28-dibenzoate de bétuline pour obtenir du 3-acétate de bétuline, (3) oxyder le 3-acétate de bétuline pour former de l'aldéhyde-3-acétate bétulinique, (4) oxyder l'aldéhyde-3-acétate bétulinique pour former du 3-acétate d'acide bétulinique, et (5) supprimer la protection du 3-acétate d'acide bétulinique pour obtenir de l'acide bétulinique.

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