Metronidazole → Metronidazole Carbonate

Reaction equation

ClC(Cl)([O:4][C:5](=[O:11])[O:6]C(Cl)(Cl)Cl)Cl.[CH3:13][C:14]1[N:18]([CH2:19][CH2:20][OH:21])[C:17]([N+:22]([O-:24])=[O:23])=[CH:16][N:15]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:13][C:14]1[N:18]([CH2:19][CH2:20][OH:21])[C:17]([N+:22]([O-:24])=[O:23])=[CH:16][N:15]=1.[C:5](=[O:4])([O-:11])[O-:6]

Participants

Procedure

mPEG11OH (0.39 mmol, 200 mg) and DMAP (0.93 mmol) were dissolved in anhydrous DCM (10 ml). Triphosgene (0.13 mmol, 38.5 mg) was added at room temperature. The solution was stirred at room temperature for ten minutes. Metronidazole (0.43 mmol, 73.5 mg) was added and the reaction solution was stirred at room temperature overnight. The solvent was evaporated at reduced pressure. The residue was subjected to flash chromatography (methanol/DCM=2˜5%) to obtain compound 2c (107 mg, yield 38%). 1H NMR (CDCl3) δ 7.92 (s, 1H), 4.55 (t, 2H), 4.45 (t, 2H), 4.21 (t, 2H), 3.66-3.49 (m, 42H), 3.33 (s, 3H), 2.47 (s, 3H). LC/MS 714 [M+H]+.