Method for manufacturing betulinic acid
AssigneesRegents of the University of Minnesota, Naturtek, LLC
InventorsPavel A. Krasutsky, Robert M. Carlson, Vitaliy V. Nesterenko
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Abstract
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.
Claims46
A process for preparing a compound of formula III
- comprising:
- (1) acylating a compound of formula I
- to provide a corresponding compound of formula II;
- and
- (2) alcoholyzing a compound of formula II to provide a corresponding compound of formula III;
- wherein R1 and R2 are each (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C6-C10)aryl, (C1-C10)alkoxy, or (C6-C10)aryl(C1-C10)alkyl;
- any alkyl, alkoxy, alkenyl, alkynyl, or aryl of R1 and R2 can optionally be substituted with one or more halo, nitro, cyano, trifluoromethyl, hydroxy, SR or NRR;
- and
- each R is independently H or (C1-C10)alkyl.
Dependencies are inferred from the claim text.