Hydrochloric Acid → N-{(1S,2R)-1-(3,5-Difluorobenzyl)-2-hydroxy-3-[(6-neopentyl-1,2,3,4-tetrahydroquinolin-4-YL)amino]propyl}acetamide

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To a solution of benzyl 4-{[(2R,3S)-3-(acetylamino)-4-(3,5-difluorophenyl)-2-hydroxybutyl]amino}-6-neopentyl-3,4-dihydroquinoline-1(2H)-carboxylate (0.242 g) in EtOH (30 mL) was added 1N HCl (1.0 mL) and 10% palladium on carbon (0.030 g). The mixture was degassed with N2 for five minutes. The mixture was placed on a hydrogenation apparatus under 47 psi of H2 and was shaken for 4.5 hours. The palladium was filtered off using Celite and the solvent was concentrated under reduced pressure. The residue was then partitioned between water and ethyl acetate and the organic layers were washed with aqueous sodium bicarbonate, dried with magnesium sulfate, filtered, and concentrated. A silica gel column using 4% MeOH in dichloromethane with 0.25% NH4OH as the solvent solution gave 0.095 g of the title compound. MS (ESI+) for C26H35F2N3O2 m/z 460.27 (M+H)+.

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