Ethyl isobutyrylacetate → Ethyl 3-amino-4-methyl-pent-2-enoate

HRID 588085Notes

Reaction equation

HRID 588085 reaction equation
[CH3:1][CH:2]([CH3:11])[C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].C([O-])(=O)C.[NH4+:16]>CO>[NH2:16][C:3]([CH:2]([CH3:11])[CH3:1])=[CH:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 81583Ethyl isobutyrylacetateHCID 517165Ammonium Acetate

Product 1

HCID 59557418Ethyl 3-amino-4-methyl-pent-2-enoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 4-methyl-3-oxopentanoate (4.5 mL, 27.9 mmol) and ammonium acetate (12.05 g, 156 mmol) in MeOH (50 mL) was stirred at room temperature overnight. The solvent was evaporated in vacuo and chloroform (50 mL) was added. The resulting solid was filtered and washed with chloroform (2×25 mL). The combined filtrate was washed with water (30 mL) and brine (30 mL), dried over Na2SO4, and concentrated in vacuo to give ethyl 3-amino-4-methylpent-2-enoate, which was carried onto the next step without further purification. MS ESI calc'd. for C8H15NO2 [M+1]+ 158. found 158.

Workup

  1. customThe solvent was evaporated in vacuo and chloroform (50 mL)
  2. additionwas added
  3. filtrationThe resulting solid was filtered
  4. washwashed with chloroform (2×25 mL)
  5. washThe combined filtrate was washed with water (30 mL) and brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b22d0bf3e44402da0d74ede6ad1db6a
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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