Pyroglutamate salts and their use in the optical resolution...

Details Pyroglutamate salts and their use in the optical resolution... Pyroglutamate salts and their use in the optical resolution...

2006-02-23

2009-11-17

Bernhardt, Emily (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C514S255040

Reexamination Certificate

active

07619085

ABSTRACT:
The present invention relates to (S)-2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide-(S)-pyrrolidone-5-carboxylic acid salt; (R)-2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide-(S)-pyrrolidone-5-carboxylic acid salt; (S)-2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide-(R)-pyrrolidone-5-carboxylicacid salt; or (R)-2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxycetamide-(R)-pyrrolidone-5-carboxylic salt. The present invention relates also to a process for preparing (S)-2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide (I) and (R)-2-[4-(4-chlorobenzhydryl) piperazin-1-yl]-ethoxyacetamide (II) by chemical resolution of a mixture. These compounds are respectively intermediates for the synthesis of dextrocetirizine and levocetirizine.

REFERENCES:
patent: 5478941 (1995-12-01), Cossement et al.
patent: 2009/0143582 (2009-06-01), Zhu
patent: 2225321 (1990-05-01), None
patent: 1994-06429 (1994-03-01), None
Pflum, Derek, A., “A Large-Scale Synthesis of Enantiomerically Pure Cetirizine Dihydrochloride Using Preparative Chiral HPLC,” Organic Process Research & Development, 2001, pp. 110-115.

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