Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2007-03-20
2007-03-20
McKane, Joseph K. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
10800741
ABSTRACT:
A process for preparing (R)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxo-1-heptanoic acid, tert-butylester comprising:(a) reduction of 5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-3-oxo-1-pentanoic acid, (R)-2-hydroxy-1,2,2-triphenylethyl ester;(b) hydrolysis of (R)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-3-hydroxy-1-pentanoic acid, (R)-2-hydroxy-1,2,2-triphenylethyl ester using an alkali base in a solvent to form the acid;(c) alkylation of the acid forming (R)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxo-1-heptanoic acid, tert-butylester.
REFERENCES:
patent: 5273995 (1993-12-01), Roth
Brooks, D.W., et al. “C-Acylation under Virtually Neutral Conditions”,Angew. Chem. Int. Ed. Engl., (1979) 18, No. 1, pp. 72-74.
Brower, P.L., et al., “The Synthesis of (4R-cis)-1,1-Dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate, a Key Intermediate for the Preparation of Cl-981, a Highly Potent, Tissue Selective Inhibitor of HMG-CoA Reductase”,Tetrahedron Letters, (1992) vol. 33, No. 17, pp. 2279-2282.
Che Daqing
Guntoori Bhaskar Reddy
Horne Stephen E.
Murthy K. S. Keshava
Wang Fan
Apotex Pharmachem Inc.
Hughes Ivor M.
Hughes Neil H.
McKane Joseph K.
Sarkis Marcelo K.
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