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Water → 2-[(4-{2-[(4-Bromobenzyl)oxy]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid ethyl ester

HRID 914341
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 914341
[CH2:1]([O:3][C:4](=[O:17])[C:5]([S:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][CH2:15][OH:16])[N:13]=1)([CH3:7])[CH3:6])[CH3:2].[Br:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1.CC(C)([O-])C.[K+].O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:17])[C:5]([S:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][CH2:15][O:16][CH2:23][C:22]2[CH:25]=[CH:26][C:19]([Br:18])=[CH:20][CH:21]=2)[N:13]=1)([CH3:7])[CH3:6])[CH3:2]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 685274-Bromobenzyl bromideHCID 23665647Potassium tert-butoxideHCID 597593272-{[4-(2-Hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid ethyl ester

Produkt 1

HCID 597590082-[(4-{2-[(4-Bromobenzyl)oxy]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid ethyl esterAusbeute 50,3 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-{[4-(2-Hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid ethyl ester (1.6 g) synthesized in Example 155-1 and 4-bromobenzylbromide (1.7 g) were dissolved in N,N-dimethylformamide (30 mL), potassium tert-butoxide (0.72 g) was added, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=10:1 to 3:1) to give the title compound (1.3 g) as a colorless oil.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=10:1 to 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-5d950c39c7fd420fb065e0738535f3e6
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08026370B2

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