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

HRID 450488Notes

Reaction equation

HRID 450488 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 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-72b539bbab76460689fcdeb12cf28e17
Source dataset
uspto-grants-2013_07
Patent number
US08486965B2

Reaction notes

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