Potassium Carbonate → HCID 21911050, Verbindung

HRID 969482

Reaktionsgleichung

Reaktionsgleichung von HRID 969482
F[C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:13](=[O:16])([O-])[O-:14].[K+].[K+].[OH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][N:33](C)[C:34](=O)OC(C)(C)C)[CH:27]=2)=[CH:22][CH:21]=1>CC(N(C)C)=O.O>[C:3]([O:14][C:13]([CH2:34][NH:33][CH2:32][C:28]1[CH:27]=[C:26]([C:23]2[CH:24]=[CH:25][C:20]([O:19][C:2]3[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=3[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:21][CH:22]=2)[CH:31]=[CH:30][CH:29]=1)=[O:16])([CH3:9])([CH3:4])[CH3:2]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 67953Benzoic acid, 2-fluoro-, ethyl esterHCID 69643261Tert-butyl(4'-hydroxybiphenyl-3-ylmethyl)methylcarbamate

Produkt 1

HCID 21911050HCID 21911050, VerbindungAusbeute 104,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

2.15 g (12.8 mmol) of ethyl 2-fluorobenzoate and 1.9 g (14 mmol) of potassium carbonate are successively added to a solution of 4 g (12.8 mmol) of tert-butyl (4′-hydroxybiphenyl-3-ylmethyl)methylcarbamate in 45 ml of dimethylacetamide. The reaction medium is refluxed for 48 hours, cooled, diluted with water and extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated under vacuum. The residue obtained is purified by chromatography on a column of silica eluted with an 80/20 heptane/ethyl acetate mixture. 3.1 g of ethyl 2-{3′-[(tert-butoxycarbonylmethylamino)methyl]biphenyl-4-yloxy}benzoate are obtained in the form of a colorless oil, in a yield of 53%.

Aufarbeitung

  1. temperatureThe reaction medium is refluxed for 48 hours
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with an 80/20 heptane/ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag
ord-cb2bf88750c64ea8856627e28cf92620
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07307078B2

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