Cesium carbonate → 4-(4-Carbamoyl-3-hydroxy-phenoxy)-butyric Acid Ethyl Ester

HRID 1368336

Reaktionsgleichung

Reaktionsgleichung von HRID 1368336
[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C=O)C.O>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19][O:11][C:9]1[CH:8]=[CH:7][C:3]([C:4](=[O:5])[NH2:6])=[C:2]([OH:1])[CH:10]=1)[CH3:26]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 76300Ethyl 4-bromobutyrateHCID 766012,4-Dihydroxybenzamide

Produkt 1

HCID 120727834-(4-Carbamoyl-3-hydroxy-phenoxy)-butyric Acid Ethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 2,4-dihydroxybenzamide (16.5 g, 108.3 mmol) in DMF (100 mL) was added Cs2CO3 (39.0 g, 119.1 mmol) followed by ethyl 4-bromobutyrate (17.0 mL, 119.1 mmol). The mixture was heated to 70 OC for 2 h, cooled, diluted with water and extracted with EtOAc. The combined extracts were washed with water, dried over magnesium sulfate, concentrated, and chomatographed over silica gel (60% EtOAc/hexane) to a white solid (4.2 g, 15%). MS [M+H]+ 267.

Aufarbeitung

  1. temperatureThe mixture was heated to 70 OC for 2 h
  2. temperaturecooled
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-78514d3877c348f3af47d47138351655
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06573295B2

Verknüpfte Notizen

Wird geladen…