Water → N-[(1,1-Dimethylethoxy)carbonyl]-N-(6-methyl-2-pyridinyl)glycine 1,1-dimethylethyl ester

HRID 2359808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2359808
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].O>CN(C)C=O>[C:23]([O:22][C:20](=[O:21])[CH2:19][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=1)([CH3:26])([CH3:25])[CH3:24]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 11367776tert-Butyl (6-methylpyridin-2-yl)carbamate

Produkt 1

HCID 86651793N-[(1,1-Dimethylethoxy)carbonyl]-N-(6-methyl-2-pyridinyl)glycine 1,1-dimethylethyl esterAusbeute 101,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(tert-butoxycarbonylamino)-6-methylpyridine (723 mg, 3.47 mmol) in N,N-dimethylformamide (11.5 ml) was added sodium hydride (mineral oil 55% dispersion) (0.18 g, 4.2 mmol) in portions under ice cooling. After stirring at room temperature for 30 minutes, tert-butyl bromoacetate (0.62 ml, 4.2 mmol) was added dropwise under ice cooling, followed by stirring at room temperature for 2 hours. After completion of the reaction, water was added to the reaction solution, followed by extraction with ethyl acetate. The separated organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=10:1→5:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (1.14 g) substantially quantitatively as a colorless liquid.

Aufarbeitung

  1. stirringby stirring at room temperature for 2 hours
  2. additionwas added to the reaction solution
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe separated organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additioncontaining the desired compound
  8. concentrationwere concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c51eee7250274980b7f9bb5bf3adbca3
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08685986B2

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