Malonic Acid → 3-amino-3-(3,4,5-trimethoxyphenyl)propanoic acid

HRID 1971324Notes

Reaction equation

HRID 1971324 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=O.[C:15]([OH:21])(=[O:20])[CH2:16]C(O)=O.C([O-])(=O)C.[NH4+:26]>CCO>[NH2:26][CH:6]([C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=1)[CH2:16][C:15]([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 68583,4,5-TrimethoxybenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 33126913-amino-3-(3,4,5-trimethoxyphenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,4,5-Trimethoxy benzaldehyde (10 mmol, 1 eq), malonic acid (1 eq) and ammonium acetate (1.3 eq) are suspended in EtOH and refluxed for 16 h (Tetrahedron, 58 (2002) 7449-7461). Upon cooling to room temperature a white precipitate is formed. The mixture is concentrated in vacuo and the white solid is partitioned between EtOAc and dilute aqueous HCl (pH 2). The aqueous phase is concentrated in vacuo. 3-Amino-3-(3,4,5-trimethoxy-phenyl)propionic acid (crude product) is obtained as a white solid (51% yield); ES-MS (MH+)=239.0 (M-NH2).

Workup

  1. temperaturerefluxed for 16 h (Tetrahedron, 58 (2002) 7449-7461)
  2. customis formed
  3. concentrationThe mixture is concentrated in vacuo
  4. customthe white solid is partitioned between EtOAc and dilute aqueous HCl (pH 2)
  5. concentrationThe aqueous phase is concentrated in vacuo

Sources & evidence

ORD record
ord-e8f28bcc60274fd58c18f2fd916b3376
Source dataset
uspto-grants-2013_04
Patent number
US08431602B2

Reaction notes

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