Dimethylformamide → Ethyl 3-[(tert-butoxycarbonyl)(2-methoxyethyl)amino]benzoate

HRID 1662055Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662055
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C=O)C.[H-].[Na+].Br[CH2:28][CH2:29][O:30][CH3:31]>C(OCC)(=O)C.O>[C:1]([O:5][C:6]([N:8]([CH2:28][CH2:29][O:30][CH3:31])[C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 24758Sodium hydride2×HCID 809722-Bromoethyl methyl ether2×HCID 22643546Ethyl 3-[(tert-butoxycarbonyl)amino]benzoate

Produkt 1

HCID 59453987Ethyl 3-[(tert-butoxycarbonyl)(2-methoxyethyl)amino]benzoateAusbeute 58,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of ethyl 3-[(tert-butoxycarbonyl)amino]benzoate (3.8 g) and DMF (20 ml) were added 60% sodium hydride (1.1 g) and 2-bromoethylmethyl ether (3.9 g) under ice-cooling, followed by stirring at room temperature over one night. To the reaction mixture were added 60% sodium hydride (0.28 g) and 2-bromoethylmethyl ether (0.98 g), followed by stirring at room temperature for 6 hours. Water and ethyl acetate were added thereto, and the organic layer was then separated, washed with 1 M hydrochloric acid and saturated brine in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain ethyl 3-[(tert-butoxycarbonyl)(2-methoxyethyl)amino]benzoate (2.7 g).

Aufarbeitung

  1. temperaturecooling
  2. stirringby stirring at room temperature for 6 hours
  3. customthe organic layer was then separated
  4. washwashed with 1 M hydrochloric acid and saturated brine in this order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-838617da2740488885246466c41f38ed
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030489B2

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