C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 207/34 (2006.01)
Patent
CA 2498978
A process is provided 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, R- substituted ester 9 comprising: (a) reacting the aldehyde 1 with the enolate form of (S)-2-hydroxy-1,2,2- triphenylethyl acetate substituent in a chelating co-solvent; See Formula 1 (b) hydrolysis of (R,S)-5-[2-{4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4- [(phenylamino)carbonyl]-1H-pyrrol-1-yl]-3-hydroxy-1-pentanoic acid, (S)-2- hydroxy-1,2,2-triphenylethyl ester (2a and 2b) using a base, preferably an alkali metal base, preferably in a solvent to form the carboxylic acid 7; See formula 2 (c) treating the acid 7 with a chiral base to form a salt and purifying the salt to obtain enantiomerically enriched (R)-7 chiral base salt; See formula 3 (d) alkylation of the (R)-7 chiral base salt or the free base derived from (R)- 7, forming (R)-S-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4- [(phenylamino)carbonyl]-1H-pyrrol-1-yl]-S-hydroxy-3-oxo-1-heptanoic acid, R- substituted ester 9 and atorvastatin calcium 6, (see formula I) wherein R is a C1 to C6 alkyl, C6 to C9 aryl or C7 to C10 aralkyl.
Che Daqing
Chow Alan
Faught Jody
Guntoori Bhaskar Reddy
Kinsman Aaron C.
Apotex Pharmachem Inc.
Mckinnon Graham J.k.
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