C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/351.1, 260/5
C07D 317/32 (2006.01) C07C 45/46 (2006.01) C07C 49/807 (2006.01) C07C 51/00 (2006.01) C07C 59/68 (2006.01) C07D 409/04 (2006.01)
Patent
CA 1282410
ABSTRACT A new enantioselective process is described for preparing optically active alpha-arylalkanoic acids by: a) halogenation on the aliphatic carbon atom alpha to the ketal group, of ketals of formula Image in which Ar represents an aryl, optionally substituted; R represents a C1-C4 alkyl; R1 and R2, represent a hydroxy, a O- M+, OR3 or NR4R5 group; the carbon atoms indicated by an asterisk both simultaneously are in (R) or (S) configuration. This reaction is diastereoselective, so that a misture of alpha- haloketals is obtained in which one of the two epimers prevails, and generally strongly prevails, over the other. b) rearrangement of the haloketals of formula Image (A) in which X is Cl, Br or I to alpha-arylalkanoic acids in a single stage or in two successive stages, by way of esters of formula Image (C) The compounds (A) and (C) are all new compounds. The rearrengement step (b) may be performed under new, inventive conditions. The esters of formula (C) have pharmacological activity analogous to that of the corresponding alpha-arylalkanoic acids.
478585
Castaldi Graziano
Cavicchioli Silvia
Giordano Claudio
Uggeri Fulvio
Castaldi Graziano
Cavicchioli Silvia
Giordano Claudio
Marks & Clerk
Uggeri Fulvio
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