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Metronidazole → Metronidazole Carbonate

HRID 533288
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HRID 533288 반응식
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]
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참가 물질

5

반응물 2

HCID 4173MetronidazoleHCID 94429Triphosgene

생성물 1

HCID 68777643Metronidazole Carbonate수율 732.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

mPEG21OH (0.21 mmol, 200 mg) and DMAP (1.0 mmol) were dissolved in anhydrous DCM (10 ml). Triphosgene (0.13 mmol, 39 mg) was added at room temperature. The solution was stirred at room temperature for 5 minutes. Metronidazole (1.0 mmol, 171 mg) was added and the reaction solution was stirred at room temperature overnight. The solvent was evaporated at reduced pressure. The residue was extracted with EtOAc/H2O (20 ml/20 ml) three times. The aqueous phases were combined and adjusted to PH 4.0 by adding 0.1N HCl solution. The solution was extracted with DCM (3×20 ml). The organic phases were combined and dried with anhydrous Na2SO4. The solid was filtered off and the solvent was evaporated to give compound 2d (220 mg, yield 90%). 1H NMR (CDCl3) δ 7.89 (s, 1H), 4.53 (t, 2H), 4.43 (t, 2H), 4.19 (t, 2H), 3.63-3.46 (m, 80H), 3.31 (s, 3H), 2.45 (s, 3H). LC/MS 1154 [M+H]+.

후처리

  1. stirringthe reaction solution was stirred at room temperature overnight
  2. customThe solvent was evaporated at reduced pressure
  3. extractionThe residue was extracted with EtOAc/H2O (20 ml/20 ml) three times
  4. additionby adding 0.1N HCl solution
  5. extractionThe solution was extracted with DCM (3×20 ml)
  6. dry with materialdried with anhydrous Na2SO4
  7. filtrationThe solid was filtered off
  8. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-ca82effe95dd454f97a69d6f9894a481
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08853247B2

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