Tetrahydrofuran → HCID 69457443, Verbindung

HRID 916084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916084
[H-].[Na+].O1CCCC1.[CH3:8][O:9][C:10](=[O:28])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][S:18][C:19]1[NH:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1.[C:29]([O:33][C:34](=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[CH2:41]Br)([CH3:32])([CH3:31])[CH3:30]>O>[CH3:8][O:9][C:10](=[O:28])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][S:18][C:19]1[N:20]([CH2:41][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[C:34]([O:33][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:43])[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 11459925Benzoic acid, 2-(bromomethyl)-, 1,1-dimethylethyl esterHCID 69456394HCID 69456394, Verbindung

Produkt 1

HCID 69457443HCID 69457443, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Sodium hydride (104 mg, 2.86 mmol) and tetrahydrofuran (16 ml) were added to a previously dried reaction vessel. To the mixture were added 2-(benzimidazole-2-ylthiomethyl)benzoic acid methyl ester (428 mg, 1.43 mmol) and 2-(bromomethyl)benzoic acid t-butyl ester (466 mg, 3.46 mmol), and then the mixture was stirred at 60° C. for 50 minutes. Water was added thereto, followed by extraction with ethyl acetate. After the ethyl acetate phase was dried with anhydrous sodium sulfate, it was concentrated, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate=3:1) to obtain 2-((1-((2-((t-butyl)oxycarbonyl)phenyl)methyl)benzimidazole-2-ylthio)methyl)benzoic acid methyl ester (495 mg, yield 71%).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialAfter the ethyl acetate phase was dried with anhydrous sodium sulfate, it
  3. concentrationwas concentrated
  4. customthe residue was purified by silica gel column chromatography (hexane: ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-7a50594bf5f04aee9226b1bb558c5956
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268145B2

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