Malonic Acid → 3-Amino-3-(pyridin-3-yl)propanoic acid

HRID 1455867Notes

Reaction equation

HRID 1455867 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1C=O.C([O-])(=O)C.[NH4+:13].[C:14](O)(=O)[CH2:15][C:16]([OH:18])=[O:17]>C(O)(C)C>[NH2:13][CH:14]([C:5]1[CH:6]=[N:1][CH:2]=[CH:3][CH:4]=1)[CH2:15][C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 142732-PyridinecarboxaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 36065473-Amino-3-(pyridin-3-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Scheme I describes a synthesis of a pyridyl β-amino acid which can be used to synthesize compounds of the present invention wherein R1 is pyridyl. The reaction can be modified using conventional methodology to prepare other aroma substituted or heterocyclic substituted β-amino acids by substitution of the pyridyl carboxaldehyde with any other appropriate aldehyde. Briefly, in Scheme I to pyridine-carboxaldehyde in isopropanol is added ammonium acetate followed by malonic acid. The reaction mixture is stirred at reflux, the resulting precipitate filtered and washed with hot isopropanol and dried to yield 3-amino-3-(3-pyridyl)propionic acid. The ethyl ester is synthesized by heating this acid in excess ethanol in the presence of excess HCl gas.

Workup

  1. customto synthesize compounds of the present invention wherein R1
  2. customThe reaction
  3. temperatureat reflux
  4. filtrationthe resulting precipitate filtered
  5. washwashed with hot isopropanol
  6. customdried

Sources & evidence

ORD record
ord-9f03cfb4887d4ed08bac0b281ef45b49
Source dataset
uspto-grants-1998_12
Patent number
US05843906

Reaction notes

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