1-((Pyrrolidine-1-carbonyl)methyl)piperazine → 5-{(4S,5R)-4,5-Bis-(4-chlorophenyl)-4,5-dimethyl-1-[4-(2-oxo-2-pyrrolidin-1-yl-ethyl)-piperazine-1-carbonyl]-4,5-dihydro-1H-imidazol-2-yl}-N-tert-butyl-2-chloro-4-ethoxybenzenesulfonamide

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Reaction Steps

In a manner analogous to the method described in example 5, rac-(4S*,5R*)-2-(5-tert-butylsulfamoyl-4-chloro-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride (example 45) was reacted with 2-piperazin-1-yl-1-pyrrolidin-1-yl-ethanone (Aldrich) to give the title compound as a racemic mixture. The enantiomers were then separated by supercritical fluid chromatography (Berger Instrument Multi-Gram II, Daicel ChiralPak OJ-H 3×25 cm, 35° C. at 100 bar, eluting with 15% methanol in carbon dioxide). HR-MS (ES, m/z) calculated for C40H50N6O5SCl3 [(M+H)+] 831.2624, observed 831.2625.

Provenance & Evidence