Ethyl Acetate → 2-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-(2-trimethylsilanyl-ethoxymethyl)-amino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazole-5-carboaldehyde

HRID 2110025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2110025
[C:1]1([CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][N:19]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:20]3[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:23]4[CH:33]=[CH:34][C:35]([CH2:37][OH:38])=[CH:36][C:22]=4[N:21]=3)[CH2:14][CH2:13]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.OI1(=O)C2C=CC=CC=2C(=O)O1.C(OCC)(=O)C>CS(C)=O>[C:1]1([CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([CH2:18][N:19]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:20]3[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:31])[CH3:32])[C:23]4[CH:33]=[CH:34][C:35]([CH:37]=[O:38])=[CH:36][C:22]=4[N:21]=3)[CH2:16][CH2:17]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 3394961-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxideHCID 69075874HCID 69075874, Verbindung

Produkt 1

HCID 230689442-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-(2-trimethylsilanyl-ethoxymethyl)-amino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazole-5-carboaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

A solution of [2-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-(2-trimethylsilanyl-ethoxymethyl)-amino]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-5-yl]-methanol (467 mg, 0.71 mmol) in dimethylsulfoxide (5 ml) was added to a solution of 297 mg of 1-hydroxy-1-oxo-1H-1λ5-benzo[d][1,2]iodoxol-3-one (1.06 mmol) in dimethylsulfoxide (5 ml), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was poured into ice water (200 ml) and stirred at room temperature for 30 minutes, after which ethyl acetate was added and stirring was continued vigorously for 10 minutes for extraction. After washing with saturated aqueous sodium bicarbonate and then with saturated brine, the mixture was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 2-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-(2-trimethylsilanyl-ethoxymethyl)-amino]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazole-5-carboaldehyde.

Aufarbeitung

  1. stirringstirred at room temperature for 30 minutes
  2. stirringstirring
  3. extractionwas continued vigorously for 10 minutes for extraction
  4. washAfter washing with saturated aqueous sodium bicarbonate
  5. dry with materialwith saturated brine, the mixture was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c051b852402b46559971481f5a865f2d
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517875B2

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