Method for selective acylation of C-2'-O-protected-10-hydroxy-ta

Details Method for selective acylation of C-2'-O-protected-10-hydroxy-ta Method for selective acylation of C-2'-O-protected-10-hydroxy-ta

1998-05-01

2000-04-11

Trinh, Ba K.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549511, C07D30514

Patent

active

060489901

ABSTRACT:
A method of acylating C-2' O-protected-10-hydroxy taxol selectively at the C-10 hydroxyl position over the C-7 hydroxy position thereof to produce C-2' O-protected taxol is accomplished first by dissolving C-2' O-protected-10-hydroxy taxol in an acceptable ether solvent therefor, such as tetrahydrofuran. A lithium salt, preferably lithium chloride, is added. A trialkylamine base or pyridine is next added, followed by the addition of an acylating agent, such as acetyl chloride. The resulting solution may be quenched, for example with ammonium chloride, to eliminate excess of the acylating agent. This solution may then be diluted with ethyl acetate to form an organic phase and an aqueous phase, with the organic phase being washed and thereafter reduced. Recrystallization and column chromatography may be employed to purify the C-2' O-protected taxol.

REFERENCES:
patent: 4924011 (1990-05-01), Denis et al.
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patent: 5015744 (1991-05-01), Holton
patent: 5229526 (1993-07-01), Holton
patent: 5675025 (1997-10-01), Sisti et al.
patent: 5688977 (1997-11-01), Sisti
"A Chemoselective Approach to Functoinalize the C-10 Position of 10-Deacetylbaccatin III Synthesis and Biological Properties of Novel C-10 Taxol Analogues", by Kant et al, Tetrahedron Letters, vol. 35, No. 31, pp. 5543-5546, (1994).

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