tert-Butanol → HCID 67360378, Verbindung

HRID 1747475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1747475
[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:15][C:16]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]3[C:17]=2[CH:18]=[CH:19][NH:20]3)[C:7]1=[O:26].C([OH:32])(C)(C)C>[Zn]>[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:15][C:16]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]3[C:17]=2[CH2:18][C:19](=[O:32])[NH:20]3)[C:7]1=[O:26]

Komponenten

4

Edukt 2

HCID 6386tert-ButanolHCID 67361638HCID 67361638, Verbindung

Produkt 1

HCID 67360378HCID 67360378, VerbindungAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23994ZincKatalysator

Versuchsvorschrift

3-[3-(6-Chloro-1H-indol-4-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-propionic acid methyl ester (248 mg, 0.64 mmol) is dissolved it tert-butanol (20 mL) at 40° C. The reaction is stirred and pyridiniumtrbromide is added portion wise over 5 minutes. The reaction is stirred for 10 minutes and concentrated in vacuo. The crude material is dissolved in acetic acid (10 mL) and zinc powder (211 mg, 3.2 mmol)is added to the reaction. The reaction is stirred at room temperature for one hour, then the solvent evaporated in vacuo. The residue is taken up in dimethyl sulfoxide and filtered. The crude material is purified by preparative reverse phase LC to give the title compound (34 mg 0.09 mmol, 36%).

Aufarbeitung

  1. additionpyridiniumtrbromide is added portion wise over 5 minutes
  2. stirringThe reaction is stirred for 10 minutes
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude material is dissolved in acetic acid (10 mL)
  5. stirringThe reaction is stirred at room temperature for one hour
  6. customthe solvent evaporated in vacuo
  7. filtrationfiltered
  8. customThe crude material is purified by preparative reverse phase LC

Quellen und Nachweise

ORD-Eintrag
ord-2874c84eeabf4447a908dee6f6c191d3
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150556B2

Notizen zur Reaktion

Wird geladen…