Methyl iodide → Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate

HRID 1183028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1183028
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][CH:14]=[CH2:15])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:16][O:11][C:10](=[O:12])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][CH:14]=[CH2:15]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 51661192-{[(Tert-butoxy)carbonyl]amino}pent-4-enoic acid

Produkt 1

HCID 10857232Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

2-tert-Butoxycarbonylamino-pent-4-enoic acid (9.3 g, 43.3 mmol) in acetone (70 mL) is treated with solid potassium carbonate (11.9 g, 86.6 mmol) followed by methyl iodide (5.4 mL, 86.6 mmol). The resulting mixture is heated to reflux for 4 h and then allowed to cool to RT. The solvent is removed in vacuo and the crude residue is dissolved in EtOAc, washed with water, saturated sodium hydrogen carbonate solution, brine, dried (MgSO4) and concentrated in vacuo. The crude residue is purified by flash chromatography (SiO2, iso-hexane:EtOAc 7:3) to afford the title compound as a light-yellow oil.

Aufarbeitung

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux for 4 h
  3. customThe solvent is removed in vacuo
  4. dissolutionthe crude residue is dissolved in EtOAc
  5. washwashed with water, saturated sodium hydrogen carbonate solution, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude residue is purified by flash chromatography (SiO2, iso-hexane:EtOAc 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-e1a3692f42c54051849daa96e7f89535
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664228B2

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