Methanol → HCID 68545756, compound

Participants

Reaction Steps

N-(3-{3-Fluoro-4-[1-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-vinyl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide (48 mg) was dissolved in 1.5 mL methanol, followed by addition of NaIO4 (54 mg) and OsO4 (0.02 mL, 2.5% in water). The solution was stirred at room temperature for 4 hours and then Celite (500 mg) was added. The resulting mixture was stirred for 30 min before it was filtered and washed with EtOAc. The organic layer was dried over Na2SO4 and purified with preparative TLC (CH2Cl2/MeOH, v/v, 10/1). The titled compound was obtained as yellow solid (8 mg). ESI MS m/z 478 (M+H). 1H NMR (400 MHz, MeCN-d3) 8.06 (t, J=8.4 Hz, 1H), 7.74 (s, 1H), 7.69 (dd, J=14.0, 2.0 Hz, 1H), 7.52 (dd, J=8.8, 2.4 Hz, 1H), 6.84 (b, 1H), 4.95-5.00 (m, 2H), 4.83-4.92 (m, 1H), 4.78 (dt, J=12.0, 2.8 Hz, 1H), 4.53 (d, J=12.8 Hz, 1H), 4.41 (dt, J=12.8, 2.0 Hz, 1H), 4.30-4.35 (m, 1H), 4.29 (dd, J=12.8, 3.2 Hz, 1H), 4.21 (t, J=9.2 Hz, 1H), 3.89 (dd, J=9.2, 6.4 Hz, 1H), 3.58-3.68 (m, 2H), 3.39 (d, J=5.2 Hz, 1H), 1.98 (s, 3H).

Provenance & Evidence