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Metronidazole → Metronidazole Carbonate

HRID 533289
ノート
印刷プレビュー

反応式

HRID 533289 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 4173MetronidazoleHCID 94429Triphosgene

生成物 1

HCID 68777643Metronidazole Carbonate収率 773.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

mPEG1 kDaOH (1.0 mmol, 1.0 g) and DMAP (2.4 mmol) were dissolved in anhydrous DCM (20 ml). Triphosgene (0.33 mmol, 99 mg) was added at room temperature. The solution was stirred at room temperature for 15 minutes. Metronidazole (1.1 mmol, 188 mg) was added and the reaction solution was stirred at room temperature for four hours. The solvent was evaporated at reduced pressure. The residue was extracted with DCM and 1N HCl solution (20 ml/20 ml) twice. The organic phases were combined and dried with anhydrous Na2SO4. The solid was filtered off and the solvent was evaporated. The residue was precipitated in ethyl ether/IPA (20 ml/10 ml). The compound 2e (590 mg, yield 50%) as solid was obtained by filtration. 1H NMR (CDCl3) δ 7.98 (s, 1H), 4.60 (t, 2H), 4.50 (t, 2H), 4.27 (t, 2H), 3.74-3.54 (m, 96H), 3.39 (s, 3H), 2.52 (s, 3H). MW 1308 [M+H]+.

後処理

  1. stirringthe reaction solution was stirred at room temperature for four hours
  2. customThe solvent was evaporated at reduced pressure
  3. extractionThe residue was extracted with DCM and 1N HCl solution (20 ml/20 ml) twice
  4. dry with materialdried with anhydrous Na2SO4
  5. filtrationThe solid was filtered off
  6. customthe solvent was evaporated
  7. customThe residue was precipitated in ethyl ether/IPA (20 ml/10 ml)

出典と根拠

ORDレコード
ord-91654e8a424b4f70a3da437e8efbedf0
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08853247B2

反応ノート

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