Methyl Carbamate → Ethyl 2-(methoxycarbonylamino)-3-methylbut-2-enoate

HRID 1429217Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1429217
[CH2:1]([O:3][C:4](=[O:10])[C:5](=O)[CH:6]([CH3:8])[CH3:7])[CH3:2].[C:11](=[O:15])([O:13][CH3:14])[NH2:12].CC1C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1>C1C=CC=CC=1>[CH3:14][O:13][C:11]([NH:12][C:5](=[C:6]([CH3:8])[CH3:7])[C:4]([O:3][CH2:1][CH3:2])=[O:10])=[O:15]

Komponenten

5

Edukt 3

HCID 11722Methyl CarbamateHCID 88406Ethyl 3-methyl-2-oxobutyrateHCID 161440Pyridine 4-methylbenzene-1-sulfonate

Produkt 1

HCID 11117085Ethyl 2-(methoxycarbonylamino)-3-methylbut-2-enoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A benzene solution (90 mL) of ethyl-3-methyl-2-oxobutanoate (4.03 g, 28.0 mmol), methyl carbamate (2.098 g, 28.0 mmol) and pyridine 4-methylbenzenesulfonate (0.70 g, 2.80 mmol) was heated to reflux in a round bottom flask equipped with a Dean-Stark trap and reflux condenser. After 44 hours of heating the mixture was cooled and then partitioned between ethyl acetate (50 mL) and brine (50 mL). The organic phase was washed with brine (2×50 mL) then dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography on silica gel (ethyl acetate-hexanes) to provide the title compound as an off white crystalline solid (1.487 g, 26%).

Aufarbeitung

  1. temperatureto reflux in a round bottom flask
  2. customequipped with a Dean-Stark trap
  3. temperaturereflux condenser
  4. temperatureAfter 44 hours of heating the mixture
  5. temperaturewas cooled
  6. custompartitioned between ethyl acetate (50 mL) and brine (50 mL)
  7. washThe organic phase was washed with brine (2×50 mL)
  8. dry with materialthen dried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by chromatography on silica gel (ethyl acetate-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9e9984fc9a904cafb173bce1e99088c6
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937150B2

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