反应详情

A solution of 53 (7.16 g, 18.69 mmol) in tetrahydrofuran (THF) (100 mL) was treated with triphenylphosphine (PPh3, 5.88 g, 22.43 mmol, 1.2 equiv) and H2O (3.6 g, 3.6 mL, 0.2 mmol, 11.0 equiv) at 25° C., and the resulting reaction mixture was warmed to 50–55° C. for 12 h. When TLC and HPLC showed the reduction reaction was complete, the reaction mixture was cooled to room temperature before the solvents were removed in vacuo. The residue was directly purified by flash column chromatography (0–15% MeOH-CH2Cl2 gradient elution) to afford the desired N-[3-(4′-Aminomethyl-2-fluoro-biphenyl-4-yl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide 54 (5.82 g, 87% yield) as off-white crystals, which were of sufficient purity to be directly used in subsequent reactions. 1H NMR (300 MHz, DMSO-d6) δ 1.85 (s, 3H, COCH3), 3.04 (br. s, 2H, NH2), 3.44 (t, 2H, J=5.4 Hz), 3.78 (m, 3H), 4.18 (t, 1H, J=9.1 Hz), 4.77 (m, 1H), 7.25–7.60 (m, 7H, aromatic-H), 8.20 (t, 1H, J=5.8 Hz, NHCOCH3). LCMS (ESI) m/e 359 (M+2H)2+.

1. customthe resulting reaction mixture
2. temperaturewas warmed to 50–55° C. for 12 h
3. customthe reduction reaction
4. customwere removed in vacuo
5. customThe residue was directly purified by flash column chromatography (0–15% MeOH-CH2Cl2 gradient elution)