Pyridine → N-[[3-[3,5-difluoro-4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

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Reaction Steps

The [[3-[3,5-difluoro-4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]azide (22.4 g, 51 mmol) was dissolved in 1 L of EtOAc and then degassed three times with N2. Next, 10% Pd-C (4.48 g, 20% by weight) was added and the solution was degassed again three times (with N2) before replacing the atmosphere with H2 (balloon). After 3 hours, the reaction was determined to be complete by TLC (20% MeOH/CHCl3, UV short wave). At this point, pyridine (8.26 mL, 102 mmol) was added, followed by treatment with acetic anhydride (9.64 mL, 102 mmol). The reaction mixture was allowed to stir overnight at room temperature. The reaction was found to be complete by TLC (20% MeOH/CHCl3, UV short wave). The reaction mixture was filtered through celite (the filter cake was washed with 500 mL EtOAc), the filtrate concentrated down to approximately 600 mL, and washed with H2O (2×500 mL) and brine (500 mL). The aqueous portions were back-extracted with more EtOAc (2×500 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated to give a yellow solid. Recrystallization of the crude product from hot CHCl3 and hexane afforded 19.167 g (83%) of the title compound as a white solid with mp 177°-179° C.

Provenance & Evidence