Tetrabutylammonium Fluoride → HCID 68548526, compound

Participants

Reaction Steps

3-[2-Fluoro-4′-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6(S)-yloxymethyl)-biphenyl-4-yl]-5(R)-hydroxymethyl-oxazolidin-2-one. To a solution of 5(R)-(tert-butyl-dimethyl-silanyloxymethyl)-3-[2-fluoro-4′-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6(S)-yloxymethyl)-biphenyl-4-yl]-oxazolidin-2-one (70 mg, 0.117 mmol) in THF (8.0 mL) was added TBAF (1.0 mL, 1.0 mmol, 1.0 M in THF). The mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with EtOAc, washed with brine, purified by flash chromatography to give the title product (36 mg, 64%) as a yellow solid. ESI MS m/z 485.3 (M+H+); 1H NMR (400 MHz, DMSO) δ 8.03 (s, 1H), 7.60 (dd, J=13.6, 2.4 Hz, 1H), 7.56-7.50 (m, 3H), 7.44-7.38 (m, 3H), 5.23 (t, J=5.6 Hz, 1H), 4.74-4.66 (m, 4H), 4.46 (d, J=12.0 Hz, 1H), 4.26-4.20 (m, 2H), 4.10 (t, J=9.2 Hz, 1H), 3.85 (dd, J=8.8, 6.0 Hz, 1H), 3.68-3.64 (m, 1H), 3.58-3.52 (m, 1H).

Provenance & Evidence