Carbonic acid di-2-pyridyl ester → (S)-5-(3-nitro-pyrazol-1-ylmethyl)-oxazolidin-2-one
Reaction equation
[NH2:1][CH2:2][C@H:3]([OH:13])[CH2:4][N:5]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[N:6]1.[C:14](=O)(OC1C=CC=CN=1)[O:15]C1C=CC=CN=1>ClCCl>[N+:10]([C:7]1[CH:8]=[CH:9][N:5]([CH2:4][C@H:3]2[O:13][C:14](=[O:15])[NH:1][CH2:2]2)[N:6]=1)([O-:12])=[O:11]Participants
4
Procedure
To a solution of (S)-1-amino-3-(3-nitro-pyrazole-1-yl)-propan-2-ol (0.65 g, 3.49 mmol) in dichloromethane (15 mL) was added di-2-pyridyl carbonate (0.76 g, 3.49 mmol). The reaction mixture was stirred at room temperature for 2 h and then diluted with dichloromethane. The organic layer was washed with a saturated sodium chloride solution and dried over magnesium sulfate. The crude product obtained after concentration, was purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% to 10% methanol/dichloromethane) to afford (S)-5-(3-nitro-pyrazol-1-ylmethyl)-oxazolidin-2-one (0.36 g, 49%) as a clear colorless oil: HR-ES-MS m/z calculated for C7H8N4O4 [M]+ 212, observed 213 [M+H]+.