Water → 2-{3-[4-(2-Methyl-2-morpholin-4-yl-propionyl)-phenylthio]-propylthiomethyl}-acrylic acid methyl ester

HRID 1838491Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1838491
[SH:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:22])[C:13]([CH3:21])([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH3:14])=[CH:8][CH:7]=1.Br[CH2:24][C:25](=[CH2:30])[C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[K+].[K+].O>CO>[CH3:29][O:28][C:26](=[O:27])[C:25]([CH2:30][S:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:22])[C:13]([CH3:14])([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[CH3:21])=[CH:8][CH:7]=1)=[CH2:24]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5210932-Propenoic acid, 2-(bromomethyl)-, methyl esterHCID 109477861-[4-(3-Mercaptopropylthio)phenyl]-2-methyl-2-morpholin-4-yl-propane-1-one

Produkt 1

HCID 538148112-{3-[4-(2-Methyl-2-morpholin-4-yl-propionyl)-phenylthio]-propylthiomethyl}-acrylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3.0 g (8.8 mmol) of 1-[4-(3-mercaptopropylthio)phenyl]-2-methyl-2-morpholin-4-yl-propane-1-one are dissolved in 1.50 ml of methanol. To the solution are successively added 1.89 g (10.6 mmol) of methyl 2-(bromomethyl)acrylate and 1.22 g (8.8 mmol) of potassium carbonate, and the reaction mixture is stirred at room temperature for 10 min. The reaction mixture is poured into water and extracted with ethyl acetate. The organic phase is washed with water, and dried over MgSO4. After distilling off the ethyl acetate, the residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:3) as an eluent, and an oily product is obtained.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over MgSO4
  4. distillationAfter distilling off the ethyl acetate
  5. customthe residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:3) as an eluent
  6. customan oily product is obtained

Quellen und Nachweise

ORD-Eintrag
ord-9a6d97723252457abe296f65fd4b13d1
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06673850B1

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