Benzoyl chloride → HCID 66936364, Verbindung

HRID 1366527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1366527
[CH3:1][C:2]([C:11]([O:13][CH3:14])=[O:12])([CH3:10])[NH:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].C([O-])(O)=O.[Na+].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl.O>[CH3:10][C:2]([C:11]([O:13][CH3:14])=[O:12])([CH3:1])[N:3]([CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])[C:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:27]

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 13601736N-(3-Methoxy-3-oxopropyl)-2-methylalanine methyl ester

Produkt 1

HCID 66936364HCID 66936364, VerbindungAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21908982Water methylene chlorideLösungsmittel

Versuchsvorschrift

To a mixture of methyl 2-methyl-N-[3-(methyloxy)-3-oxopropyl]alaninate (11.71 g, 57.62 mmol) in 1:1 DCM-water (300 mL) was added NaHCO3 (9.68 g, 115.2 mmol) followed by benzoyl chloride (7.02 mL, 60.48 mmol). The mixture was vigorously stirred overnight, and the phases were then separated. The organic phase was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (35% EtOAc in hexanes) to give methyl 2-methyl-N-[3-(methyloxy)-3-oxopropyl]-N-(phenylcarbonyl)alaninate (3.6787 g, 21% yield) as a colorless oil. LCMS: (M+H)+: 308.1.

Aufarbeitung

  1. customthe phases were then separated
  2. dry with materialThe organic phase was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (35% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-5cee7f025c1b40e1a37faa883739ee64
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893056B2

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