Benzyl Bromide → Diethyl 2-benzyl-2-(tert-butoxycarbonylamino)malonate

HRID 1526508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1526508
[CH2:1]([O:3][C:4](=[O:19])[CH:5]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[O-]CC.[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)C>[CH2:9]([O:8][C:6](=[O:7])[C:5]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([NH:11][C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[C:4]([O:3][CH2:1][CH3:2])=[O:19])[CH3:10]

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 382219Diethyl 2-((tert-butoxycarbonyl)amino)malonateHCID 2723922Sodium ethoxide

Produkt 1

HCID 59685129Diethyl 2-benzyl-2-(tert-butoxycarbonylamino)malonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To diethyl[(tert-butoxycarbonyl)amino]propanedioate (5.56 mL, 21.79 mmol) in ethanol (30 ml) was added sodium ethoxide (9.76 ml, 26.2 mmol) followed by benzyl bromide (2.59 mL, 21.79 mmol). The mixture was stirred for 6 h, and the solvent was removed in vacuo. Saturated aqueous sodium hydrogen carbonate (50 mL) was added and the mixture was extracted with ethyl acacate (3×50 mL). The combined organic fractions were washed with saturated aqueous brine (1×50 mL), dried with anhydrous sodium sulfate, filtered and the solvent removed in vacuo to afford the title compound as a colorless amorphous solid. LC/MS 366.1 (M+1).

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. additionSaturated aqueous sodium hydrogen carbonate (50 mL) was added
  3. extractionthe mixture was extracted with ethyl acacate (3×50 mL)
  4. washThe combined organic fractions were washed with saturated aqueous brine (1×50 mL)
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-33d59f4ce0474381aa03b4ac87ce8f3f
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085568B2

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