Use of fluorine-containing stationary phases for the separation of an alkyl bromide from its hydrocarbon analog by high-performance liquid chromatography.
Radiolabelled Sch 13835, an inhibitor of platelet derived growth factor, was prepared by catalytic hydrogenolysis of a benzyl bromide precursor with tritium gas. Regular and deactivated reversed-phase HPLC stationary phases gave poor peak shapes and little resolution of Sch 13835 and the benzyl bromide precursor. Fluorodecyl and fluoroether stationary phases in the analytical reversed-phase mode gave baseline separation using organic-aqueous (no buffers) mobile phases. Elution orders were reversed on either phase by a change in the organic component from methanol to acetonitrile. The product is unstable in aqueous (or other protic) solvents, forming a ring-opened acid. Conditions were developed to successfully purify the compound by reversed-phase HPLC with minimal decomposition. A second analytical HPLC assay was developed using normal-phase solvents on a fluoroether stationary phase.
Hendershot
S
S
Schering-Plough Research Institute, Kenilworth, NJ 07033, USA.
Koharski
D
D
McNamara
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P
D002722:Chlorobenzenes / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D005461:Fluorine / Q000737:chemistry*; D010797:Phthalimides / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification*; D013056:Spectrophotometry, Ultraviolet; D013449:Sulfonamides / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification*; D014316:Tritium
D002722:Chlorobenzenes; D010797:Phthalimides; D013449:Sulfonamides; D014316:Tritium; C106033:SCH 13835; C088156:2-bromomethyl-5-chlorobenzene sulfonylphthalimide; D005461:Fluorine