Displacement chromatography on cyclodextrin silicas. IV. Separation of the enantiomers of ibuprofen.
A displacement chromatographic method has been developed for the preparative separation of the enantiomers of ibuprofen using a beta-cyclodextrin silica stationary phase. The retention behavior of ibuprofen was studied in detail: the log k' vs. polar organic modifier concentration, the log k' vs. pH, the log k' vs. buffer concentration and the log k' vs. 1/T relationships; also, the alpha vs. polar organic modifier concentration, the alpha vs. pH, the alpha vs. buffer concentration and the log alpha vs. 1/T relationships have been determined in order to find the carrier solution composition which results in maximum chiral selectivity and sufficient, but not excessive solute retention (1 < k' < 30). 4-tert.-Butylcyclohexanol, a structurally similar but more retained compound than ibuprofen, was selected as displacer for the separation. Even with an alpha value as small as 1.08, good preparative chiral separations were observed both in the displacement mode and in the overloaded elution mode, up to a sample load of 0.5 mg.
Farkas
G
G
Department of Chemistry, Texas A and M University, College Station 77843-3255.
Irgens
L H
LH
Quintero
G
G
Beeson
M D
MD
al-Saeed
A
A
Vigh
G
G
D000097:Acetonitriles; D002021:Buffers; D002845:Chromatography; D003505:Cyclodextrins; D005021:Ethylamines; D006863:Hydrogen-Ion Concentration; D007052:Ibuprofen / Q000737:chemistry / Q000302:isolation & purification*; D012822:Silicon Dioxide; D012997:Solvents; D013237:Stereoisomerism; D013696:Temperature
D000097:Acetonitriles; D002021:Buffers; D003505:Cyclodextrins; D005021:Ethylamines; D012997:Solvents; D012822:Silicon Dioxide; C016162:triethylamine; D007052:Ibuprofen