C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
C07C 57/30 (2006.01) C07B 57/00 (2006.01) C07C 51/487 (2006.01) C07C 57/58 (2006.01)
Patent
CA 2150355
A process is disclosed for the production of a product which is enriched in a desired enantiomer of a phenylpropionic acid selected from ibuprofen and flurbiprofen, or their pharmaceutically acceptable salts, which comprises the following stages: (a) a resolution stage, in which an o-methylbenzylamine salt of the phenylpropionic acid is prepared which is enriched in the desired enantiomer by contacting, in a mixture of toluene and methanol as solvent, a substantially racemic mixture of the phenylpropionic acid with an enantiomer of n- methylbenzylamine, the respective molar ratio of the substantially racemic phenylpropionic acid to the n-methylbenzylamine being in the range of about 1:0.25 to about 1:1; (b) a recrystallisation stage, in which the resulting enriched salt is recrystallised from a mixture of methanol and toluene to give an n-methylbenzylamine salt of the phenylpropionic acid which is further enriched in the desired enantiomer, (c) an optional liberation stage, in which the phenylpropionic acid which is further enriched in the desired enantiomer is liberated from the recrystalised salt; (d) an optional salt-preparation stage in which a solid salt of the phenylpropionic acid further enriched in the desired enantiomer is isolated, the solid salt optionally being even further enantiomerically enriched in the desired enantiomer. The desired enantiomer is preferably the (S)-enantiomer, preferred salts are the n- methylbenzylamine, lysine and sodium salts.
Coe Paul Frederick
Hardy Robert
Hirst Adrian
O'donnell Hugh Owen
Aesica Pharmaceuticals Ltd.
Mccarthy Tetrault Llp
The Boots Company Plc
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