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

HRID 1947111Notes

Reaction equation

HRID 1947111 reaction equation
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]

Participants

4

Reactant 2

HCID 121699Methyl 3-oxovalerateHCID 517165Ammonium Acetate

Product 1

HCID 21343688Methyl (2Z)-3-amino-2-pentenoateYield 18,415.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3-oxovalerate (75.0 g, 576 mmol), ammonium acetate (222 g, 2.88 mmol) and methanol (750 mL) was stirred at room temperature for 3 days. The mixture was concentrated 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.

Workup

  1. concentrationThe mixture was concentrated 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

Sources & evidence

ORD record
ord-9c88bd28a5dc47e6908e649ae605831a
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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