Sodium Chloride → ethyl 2-[(2-{(1R,2R,5S)-2-[(1E)-5-cyclohexyl-4-hydroxy-4-methyl-1-pentenyl]-5-hydroxycyclopentyl}ethyl)thio]-1,3-thiazole-4-carboxyl ate

HRID 1888312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1888312
[CH:1]1([CH2:7][C:8]([OH:30])([CH3:29])[CH2:9]/[CH:10]=[CH:11]/[C@H:12]2[CH2:16][CH2:15][C@H:14]([OH:17])[C@@H:13]2[CH2:18][CH2:19][S:20][C:21]2[S:22][CH:23]=[C:24]([C:26]([OH:28])=[O:27])[N:25]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[CH3:38][CH3:39].[Cl-].[Na+]>CN(C)C=O>[CH:1]1([CH2:7][C:8]([OH:30])([CH3:29])[CH2:9]/[CH:10]=[CH:11]/[C@H:12]2[CH2:16][CH2:15][C@H:14]([OH:17])[C@@H:13]2[CH2:18][CH2:19][S:20][C:21]2[S:22][CH:23]=[C:24]([C:26]([O:28][CH2:38][CH3:39])=[O:27])[N:25]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 18513229Ethane;iodideHCID 668587942-[(2-{(1R,2R,5S)-2-[(1E)-5-cyclohexyl-4-hydroxy-4-methyl-1-pentenyl]-5-hydroxycyclopentyl}ethyl)thio]-1,3-thiazole-4-carboxylic acid

Produkt 1

HCID 68771064ethyl 2-[(2-{(1R,2R,5S)-2-[(1E)-5-cyclohexyl-4-hydroxy-4-methyl-1-pentenyl]-5-hydroxycyclopentyl}ethyl)thio]-1,3-thiazole-4-carboxyl ate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the compound 50 in N,N-dimethylformamide (10 mL) were added potassium carbonate (1.20 g) and ethane iodide (0.350 mL) at 0° C. and the solution was stirred at room temperature for 3 Hours. To the reaction solution was added an aqueous saturated sodium chloride solution and the solution was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1) to give the title compound (1.03 g) having the following physical data.

Aufarbeitung

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-6fa9b08eea394b718b30f590a12e5a01
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501793B2

Notizen zur Reaktion

Wird geladen…