Metronidazole → Metronidazole Carbonate

HRID 589548

Reaction equation

HRID 589548 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 279.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

mPEG3OH (1.0 mmol, 164 mg) and DMAP [4-(dimethylamino)pyridine, 2.4 mmol] were dissolved in anhydrous DCM (dichloromethane, 20 ml). Triphosgene (0.34 mmol, 99 mg) was added at room temperature. The solution was stirred at room temperature for 15 minutes. Metronidazole (1.0 mmol, 171 mg) was added and the reaction solution was stirred at room temperature for two hours. The solvent was evaporated at reduced pressure. The residue was subjected to flash chromatography (methanol/DCM=2˜5%) to obtain compound 2a (220 mg, yield 61%). 1H NMR (CDCl3) δ 7.99 (s, 1H), 4.61 (t, 2H), 4.50 (t, 2H), 4.28 (t, 2H), 3.73-3.40 (m, 10H), 3.40 (s, 3H), 2.53 (s, 3H). LC/MS 362 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-ac1b3506ba594b66adb1411fc77b742e
Source dataset
uspto-grants-2016_01
Patent number
US09233932B2

Linked notes

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