Trifluoroacetic acid → HCID 21957321, compound

Participants

Reaction Steps

TFA (10 mL) is added with stirring to a solution of 4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2,6-difluoro-benzoic acid tert-butyl ester (1.44 g, 3.88 mmol) in DCM (20 mL). The resulting solution is stirred for 1 h, and the volatiles removed under vacuum to afford 4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2,6-difluoro-benzoic acid as a white solid (1.20 g). The acid intermediate is dissolved in dry t-BuOH (15 mL). Diphenylphosphoryl azide (1 mL, 4.65 mmol) and TEA (1.62 mL, 11.64 mmol) are added. The mixture is heated at reflux for 3 h and allowed to cool down to r.t. Solvent is removed under vacuum. The compund, N-[3-(4-tert-butoxycarbonylamino-3,5-difluoro-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide, is purified by silica gel column chromatography (eluent—EtOAc). The compound is dissolved in DCM (20 mL); and TFA (10 mL) is added. The reaction is stirred at r.t. for 1 h, and the volatiles are removed under vacuum. The crude aniline is purified by silica gel column chromatography (EtOAc) to afford the pure title compound. MS (m/z): 286 [M+H]+. 1H NMR (300 MHz, CDCl3) δ 2.16 (s, 3H), 3.73–3.74 (m, 2H), 3.90–3.96 (m, 1H), 4.26 (t, J=9.0 Hz, 1H), 4.93–5.01 (m, 1H), 7.32 (d, 8.7 Hz, 2H).

Provenance & Evidence