Hydrochloric Acid → HCID 15229448, Verbindung

HRID 486089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486089
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16]C)=[CH:13][CH:14]=3)[C:9]([CH3:18])=[C:8]2[CH2:19][C:20]([CH3:25])([CH3:24])[C:21]([OH:23])=[O:22])=[CH:4][CH:3]=1.[CH2:28](S)C.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[C:9]([CH3:18])=[C:8]2[CH2:19][C:20]([CH3:25])([CH3:24])[C:21]([O:23][CH3:28])=[O:22])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 117408193-[1-(4-Chlorobenzyl)-3-methyl-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid

Produkt 1

HCID 15229448HCID 15229448, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1.05 g (2.7 mmol) of 3-[1-(4-chlorobenzyl)-3-methyl-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid (EP 166,591, Example 22) and 800 μL of ethanethiol (10 mmol) in 20 mL of CH2Cl2 at -20° C. was added in portions 2.17 g (16 mmol) of AlCl3. The reaction turned light orange and was stirred at room temperature overnight. In the morning, the reaction was completed (tlc) and it was poured into a solution of 1N HCl and extracted 3× with CH2Cl2. The combined organic layers were washed with brine, dried (MgSO4), and filtered. The filtrate was evaporated and to the residual syrup (680 mg) was added 20 mL of Et2O followed by an ethereal solution of diazomethane. Evaporation of the solvent left the crude title compound which was used without further purification.

Aufarbeitung

  1. extractionextracted 3× with CH2Cl2
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated and to the residual syrup (680 mg)
  6. additionwas added 20 mL of Et2O
  7. customEvaporation of the solvent
  8. waitleft the crude title compound which
  9. customwas used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-237c7954ddd348c08e84a52307a76689
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290798

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