Metronidazole → Metronidazole Carbonate

HRID 533286

Reaktionsgleichung

Reaktionsgleichung von HRID 533286
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]

Komponenten

5

Edukt 2

HCID 4173MetronidazoleHCID 94429Triphosgene

Produkt 1

HCID 68777643Metronidazole CarbonateAusbeute 279,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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]+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-4483eec2b0eb4e9dad50219571c6765c
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853247B2

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