Triethylamine → HCID 44242680, compound

Participants

Reaction Steps

To an oven dried round bottom flask was charged 2-Nitro-6(S)-prop-2-ynyloxy-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (75 mg, 0.34 mmol), N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5(S)-ylmethyl]-acetamide (127 mg, 0.34 mmol), PhCl2(PPh3)2 (23 mg, 0.02 mmol) and CuI (3.2 mg, 0.017 mmol). The flask was flushed with nitrogen before degassed DMF (4 mL) and Et3N (0.15 mL, 1.05 mmol) were added. The resultant mixture was stirred at 80° C. for one hour before it was cooled down and partitioned into 50 mL EtOAc/50 mL water. The organic layer was washed with brine and dried over Na2SO4. Column chromatography (CH2Cl2/MeOH, v/v, 20:1 to 10:1) of the concentrated residue gave the titled compound (60 mg) as yellow solid. ESI MS m/z 474 (M+H). 1H NMR (400 MHz, MeCN-d3) 7.73 (s, 1H), 7.65 (dd, J=12.4, 2.4 Hz, 1H), 7.59 (t, J=8.4 Hz, 1H), 7.39 (dd, J=8.8, 2.4 Hz, 1H), 6.84 (b, 1H), 4.20-4.99 (m, 1H), 4.76 (dt, J=12.4, 2.8 Hz, 1H), 4.67 (s, 2H), 4.53 (d, J=12.8 Hz, 1H), 4.45-4.51 (m, 1H), 4.26-4.42 (m, 2H), 4.17 (t, J=9.2 Hz, 1H), 3.85 (dd, J=9.6, 5.2 Hz, 1H), 3.56-3.68 (m, 2H), 1.98 (s, 3H).

Provenance & Evidence