Methyl 3-oxovalerate → Methyl (2Z)-3-amino-2-pentenoate

HRID 450488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 450488
O=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].C([O-])(=O)C.[NH4+:14]>CO>[NH2:14]/[C:2](/[CH2:8][CH3:9])=[CH:3]\[C:4]([O:6][CH3:7])=[O:5]

Komponenten

4

Edukt 2

HCID 121699Methyl 3-oxovalerateHCID 517165Ammonium Acetate

Produkt 1

HCID 21343688Methyl (2Z)-3-amino-2-pentenoateAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of methyl 3-oxovalerate (75.0 g, 576 mmol), ammonium acetate (222 g, 2.88 mol) and methanol (750 mL) was stirred at room temperature for 3 days. After concentration under reduced pressure, water (500 mL) was added to the residue and the mixture was extracted with ethyl acetate (200 mL). The extract was washed with brine, dried over magnesium sulfate, concentrated under reduced pressure, and dried to give the title compound (68.5 g, 92%) as a pale-yellow oil.

Aufarbeitung

  1. concentrationAfter concentration under reduced pressure, water (500 mL)
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate (200 mL)
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-72b539bbab76460689fcdeb12cf28e17
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486965B2

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