Metronidazole → Metronidazole Carbonate

HRID 533287

Reaction equation

HRID 533287 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

5

Reactant 2

HCID 4173MetronidazoleHCID 94429Triphosgene

Product 1

HCID 68777643Metronidazole CarbonateYield 356.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

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]+.

Workup

  1. stirringthe reaction solution was stirred at room temperature overnight
  2. customThe solvent was evaporated at reduced pressure

Sources & evidence

ORD record
ord-98f760f30c594d7085976049b2895f87
Source dataset
uspto-grants-2014_10
Patent number
US08853247B2

Linked notes

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