Metronidazole → Metronidazole Carbonate

HRID 589549Notes

Reaction equation

HRID 589549 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 mind, 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-99356c08b5ae4b5f8a10432478eb7672
Source dataset
uspto-grants-2016_01
Patent number
US09233932B2

Reaction notes

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