Ammonium Acetate → Methyl 3-amino-4-methylpent-2-enoate

HRID 573003Notes

Reaction equation

HRID 573003 reaction equation
[C:1]([O-])(=O)C.[NH4+:5].[CH3:6][CH:7]([CH3:14])[C:8](=O)[CH2:9][C:10]([O-:12])=[O:11]>CO>[NH2:5][C:8]([CH:7]([CH3:14])[CH3:6])=[CH:9][C:10]([O:12][CH3:1])=[O:11]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 22019185HCID 22019185, compound

Product 1

HCID 70700467Methyl 3-amino-4-methylpent-2-enoateYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

A 2 L jacketed reactor is charged ammonium acetate (668 g, 8.67 mol) and the reactor is flushed with argon. Then 4-methyl-3-oxopentanoate (500 g, 3.47 mols) is charged followed by methanol (1.0 L). The mixture is agitated at 55° C. for 5 h and concentrated in vacuo to about 1 L and then cooled to about 20° C. A solution of iPrAc (1.5 L) is added and the organic phase is washed with water (2×1.0 L). The organic phase is concentrated to provide methyl 3-amino-4-methylpent-2-enoate (Int-2) as yellow oil (560 g, 68 wt %) in 76% yield, which is used directly in next step.

Workup

  1. customthe reactor is flushed with argon
  2. concentrationconcentrated in vacuo to about 1 L
  3. temperaturecooled to about 20° C
  4. additionA solution of iPrAc (1.5 L) is added
  5. washthe organic phase is washed with water (2×1.0 L)
  6. concentrationThe organic phase is concentrated

Sources & evidence

ORD record
ord-c4a46461541c49b084c6561047eb17b6
Source dataset
uspto-grants-2015_05
Patent number
US09029540B2

Reaction notes

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