Hydrazine hydrate (1:1) → N-(((5S)-3-(4-ethynyl-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl)methyl)acetamide

Participants

Reaction Conditions

Reaction Steps

A 50° C. suspension of Example 3A (1.65 g) in 1:1 THF/ethanol (34 mL) was treated with hydrazine monohydrate (3×240 μL) at 1 hour intervals. One hour after the final addition the mixture was cooled to 25° C. and filtered. The filtrate was concentrated in vacuo. The resultant material was dissolved in a mixture of pyridine (17 mL) and dichloromethane (17 mL), cooled to −5° C., and treated with acetic anhydride (854 μL). The reaction mixture was warmed to room temperature, stirred for 5 minutes, and concentrated to provide crude product. The crude product was dissolved in 4:1 THF/dichloromethane (75 mL) and washed with 1:1 brine/water. The aqueous wash was extracted with dichloromethane (25 mL), and the combined extracts were dried over MgSO4. Next the mixture was filtered and concentrated. The residue was dissolved in acetone (20 mL) and filtered. The filtrate was concentrated and the residue triturated with hexanes to provide the desired product. MS (ESI(+)) m/e 277 (M+H)+; 1H NMR (300 MHz, CDCl3) δ 7.5-7.4 (m, 2H), 7.16-7.19 (dd, J=2.4, 8.4 Hz, 1H), 5.93 (bt, 1H), 4.8 (m, 1H), 4.05 (t, J=9 Hz, 1H), 3.8-3.6 (m, 3H), 3.28 (s, 1H), 2.02 (s, 3H).

Provenance & Evidence