Sodium hydride → HCID 44627113, compound

Participants

Reaction Steps

A stirred solution of (6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-01 (41) (reported in U.S. Pat. No. 5,668,127 via 4 steps, starting from 2,4-dinitroimidazole and tert-butyldimethylsilyl (S)-glycidyl ether) (342 mg, 1.85 mmol) and bromide 39 (741 mg, 2.03 mmol) in anhydrous DMF (7 mL) under N2 at 0° C. was treated with 60% NaH (111 mg, 2.78 mmol), then quickly degassed and resealed under N2. After stirring at room temperature for 3 h, the reaction was cooled (CO2/acetone), quenched with ice/aqueous NaHCO3 (20 mL), added to brine (80 mL) and extracted with CH2Cl2 (6×80 mL). The combined extracts were evaporated to dryness and the residue was chromatographed on silica gel, eluting with CH2Cl2, to give 1 (694 mg, 80%) as a light yellow solid: mp (CH2Cl2/pentane) 80-82° C.; 1H NMR (CDCl3) δ 7.45-7.35 (m, 6H), 7.34 (d, J=8.5 Hz, 1H), 7.20 (m, 1H), 4.79 (d, J=12.0 Hz, 1H), 4.68 (d, J=12.1 Hz, 1H), 4.65 (ddd, J=12.1, 2.9, 2.5 Hz, 1H), 4.37 (br d, J=11.8 Hz, 1H), 4.24-4.12 (m, 3H). Anal. (C20H15ClF3N3O5) C, H, N.

Provenance & Evidence