Facile method for synthesizing baccatin III compounds

Details Facile method for synthesizing baccatin III compounds Facile method for synthesizing baccatin III compounds

2007-03-06

2007-03-06

Seaman, Margaret D. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

11127234

ABSTRACT:
A process for synthesizing a C-7 protected baccatin III compound represented by formula (A), which comprises reacting a 10-deacetylbaccatin III compound represented by formula (B) with a protecting agent and an acylating agent in the presence of a secondary amine and a nitrogen-containing compound. Also, a process for synthesizing a C-7 protected 10-deacetylbaccatin III compound represented by formula (C), which comprises reacting a 10-deacetylbaccatin III compound represented by formula (B) with a protecting agent in the presence of a secondary amine and a nitrogen-containing compound. In both processes the nitrogen-containing compound is selected from a nitrogen-containing heterocycle or a trialkylamine. When the nitrogen-containing heterocycle is selected, it may be an unsubstituted or a substituted pyridine or an unsubstituted or a substituted pyrazine. When a trialkylamine is selected, it may be, for example, triethylamine or diisopropylethylamine.wherein PG1represents the organic residue of the protecting agent, PG2represents the organic residue of the acylating agent, and R represents a simple or substituted aryl group or a heterocyclic group.

REFERENCES:
patent: 6706896 (2004-03-01), Holton et al.
patent: 99/09021 (1999-02-01), None
Holton et al., Tetrahedron Letters, “selective Protection of the C(7) and C(10) Hydroxyl Groups in 10-Deacetyl Baccatin III”, vol. 39, pp. 2883-2886.
Damen et al., Herba Polonica, “Direct conversion of 10-Deacetylbaccatin III into baccatin III as a useful synthetic tool for a high yield paclitaxel semisynthesis”, vol. 44, pp. 238-242.
International Search Report and Written Opinion dated Sep. 19, 2005.

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