Malonic Acid → 3-Amino-3-biphenyl-4-yl-propionic acid

HRID 398324Notes

Reaction equation

HRID 398324 reaction equation
[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]([OH:21])(=[O:20])[CH2:16]C(O)=O.C([O-])(=O)C.[NH4+:26]>COC(O)C>[NH2:26][CH:11]([C:10]1[CH:13]=[CH:14][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][CH:9]=1)[CH2:16][C:15]([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 109991613-Amino-3-biphenyl-4-yl-propionic acid

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Conditions

Temperature
80 °C

Procedure

18.2 g of 4-phenylbenzaldehyde, 10.4 g of malonic acid and 15.4 g of ammonium acetate in 150 ml of methoxyethanol are mixed together. After heating overnight at 80° C., the mixture is cooled and the product formed is then washed with ethanol, with ether and then dried. After washing again with water, the product is recrystallized from a methanol/water mixture with a small amount of HCl. A mixture of the expected product and of the methyl ester hydrochloride of 3-amino-3-biphenyl-4-ylpropionic acid is obtained, which is used without further purification in the following step.

Workup

  1. temperaturethe mixture is cooled
  2. customthe product formed
  3. washis then washed with ethanol, with ether
  4. customdried
  5. washAfter washing again with water
  6. customthe product is recrystallized from a methanol/water mixture with a small amount of HCl
  7. additionA mixture of the expected product

Sources & evidence

ORD record
ord-110a9237f4de4b9cbd259037e86dea3b
Source dataset
uspto-grants-2003_08
Patent number
US06610882B2

Reaction notes

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