Potassium Carbonate → Ethyl 7-[methyl-[2-[(2,2,2-trifluoroacetyl)amino]ethyl]amino]heptanoate

HRID 1356453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1356453
[F:1][C:2]([F:11])([F:10])[C:3]([NH:5][CH2:6][CH2:7][NH:8][CH3:9])=[O:4].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:9][N:8]([CH2:7][CH2:6][NH:5][C:3](=[O:4])[C:2]([F:10])([F:11])[F:1])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 122490Ethyl 7-bromoheptanoateHCID 107022842,2,2-trifluoro-N-[2-(methylamino)ethyl]acetamide

Produkt 1

HCID 18508347Ethyl 7-[methyl-[2-[(2,2,2-trifluoroacetyl)amino]ethyl]amino]heptanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2,2,2-trifluoro-N-[2-(methylamino)ethyl]acetamide (5 g) in DMF (50 ml) were added ethyl 7-bromoheptanoate (3.6 ml) and potassium carbonate (7.7 g) and stirring was continued at room temperature for 18 hr. Potassium carbonate was removed by filtration and saturated aqueous sodium bicarbonate and water was added to the filtrate, which was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride sequentially, dried with sodium sulfate, and concentrated. The residue was dissolved in toluene and purified by passing through the silica gel column (eluent; hexane to hexane-ethyl acetate (4:1) to ethyl acetate) to obtain the titled compound as a crude material (7 g).

Aufarbeitung

  1. customPotassium carbonate was removed by filtration and saturated aqueous sodium bicarbonate and water
  2. additionwas added to the filtrate, which
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride sequentially
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in toluene
  8. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-5233f0b68a1c48e59968bcdd34eefbb1
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586475B1

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