Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1996-03-19
1997-11-18
Reamer, James H.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D30514
Patent
active
056889771
ABSTRACT:
A method of producing docetaxel comprises the esterification of C7, C10 di-CBZ 10-deacetyl baccatin III and an N-CBZ C2'-protected 3-phenyl isoserine side chain wherein C2' is protected by a hydrogenatable benyl-type protecting group. The C7, C10 carbobenzyloxy groups are then replaced with hydrogen and the carbobenzyloxy group at the C3' nitrogen site is replaced with t-butoxycarbonyl. Finally, the resulting compound is deprotected at C2' by replacing the benzyl-type protecting group with hydrogen to produce docetaxel. The esterification preferably employs an excess, such as six equivalents, of the side chain for each equivalent of the C7, C10 di-CBZ 10-deacetyl baccatin III. Benzyloxymethyl is the preferred protecting group at C2'.
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Sisti Nicholas J.
Swindell Charles S.
Bryn Mawr College
Henson Michael R.
Martin Timothy J.
NaPro BioTherapeutics, Inc.
Reamer James H.
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