Potassium Carbonate → Methyl 2-[(4-{2-[benzyl(hexyl)amino]-2-oxoethyl}-2-fluorophenoxy)methyl]benzoate

HRID 2111989

Reaktionsgleichung

Reaktionsgleichung von HRID 2111989
[CH2:1]([N:8]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:9](=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:18])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][O:27][C:28](=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:8]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:9](=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:35][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[C:28]([O:27][CH3:26])=[O:37])=[C:13]([F:18])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 68871257N-Benzyl-2-(3-fluoro-4-hydroxyphenyl)-N-hexylacetamide

Produkt 1

HCID 68869229Methyl 2-[(4-{2-[benzyl(hexyl)amino]-2-oxoethyl}-2-fluorophenoxy)methyl]benzoateAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

N-benzyl-2-(3-fluoro-4-hydroxyphenyl)-N-hexylacetamide (142 mg, 0.414 mmol), 2-bromomethylbenzoic acid methyl ester (99.4 mg, 0.434 mmol) and potassium carbonate anhydrous (86 mg, 0.620 mmol) were mixed in acetonitrile (5 ml). The mixture was heated to reflux overnight and then evaporated to dry. Ethyl acetate and water were added and the two phases were separated. The organic phase was washed with brine and dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using DCM, MeOH/DCM (0.5:99.5) as eluant gave 144 mg the desired product, yield 71%.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customevaporated
  4. customto dry
  5. additionEthyl acetate and water were added
  6. customthe two phases were separated
  7. washThe organic phase was washed with brine
  8. dry with materialdried (magnesium sulphate)
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3bb747eb86d4421ebbb6e3bdcebfb2e9
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07521461B2

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