Preparative-scale separation of enantiomers of chiral...

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof

Reexamination Certificate

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C562S401000, C562S402000, C562S400000, C562S405000, C562S579000

Reexamination Certificate

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08076511

ABSTRACT:
High yields and purity are obtained in the purification of enantiomers of chiral carboxylic acids by preparative-scale chromatography by including a tertiary alcohol in the mobile phase in conjunction with an acidic modifier and a hydrophobic solvent. The tertiary alcohol is superior to other, more commonly used alcohols by reducing the extent of esterification of the enantiomer that otherwise lowers the yield and the purity.

REFERENCES:
patent: 5484530 (1996-01-01), Pirkle et al.
patent: 6333426 (2001-12-01), Moller et al.
patent: WO 2006/011047 (2006-02-01), None
patent: WO 2006011047 (2006-02-01), None
Cia, Xiaojun et al.; “Enantioseparation of acidic compounds on chiral stationary phase by high performance liquid chromatography”; 2004,Fenxi Huaxue, vol. 32, No. 2, pp. 134-138.
Miller, Larry et al.; “Chromatographic resolution of the enantiomers of a pharmaceutical intermediate from the milligram to the kilogram scale”; 1999,Journal of Chromatography, vol. 849, pp. 309-317.
Xiaojun, Cai et al.; “Enahtioseparation of acidic compounds in chiral stationary phase by high performance liquid chromatography”; 2004,Chinese Journal of Analytical Chemistry, vol. 32, No. 2, pp. 134-138.

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