Malonic Acid → 3-Amino-3-(3-nitrophenyl)propanoic acid

HRID 1368910Notes

Reaction equation

HRID 1368910 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([OH:18])(=[O:17])[CH2:13]C(O)=O.C([O-])(=O)C.[NH4+:23]>C(O)C>[NH2:23][CH:7]([C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH2:13][C:12]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 74493-NitrobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 2373203-Amino-3-(3-nitrophenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.06 mmol of 3-nitrobenzaldehyde, 5.72 g of malonic acid, 8.5 g of ammonium acetate and 40 ml of ethanol are boiled under reflux for 8 hours and stirred at room temperature overnight. The cooled reaction mixture is then filtered with suction, washed with ethanol and ether and dried in air. 3-amino-3-(3-nitrophenyl)propionic acid is obtained. Subsequent N-acylation with phenylacetyl chloride under standard conditions produces 3-(3-nitrophenyl)-3-phenylacetyl-aminopropionic acid. This racemate is dissolved in 40 ml of water, and the solution is adjusted to pH 7.5 with potassium hydroxide. The enzyme penicillin amidase is added and shaken for 3 days. Removal of the enzyme by filtration and the usual workup result in (R)-3-amino-3-(3-nitrophenyl)propionic acid and (S)-3-(3-nitrophenyl)-3-phenylacetylaminopropionic acid.

Workup

  1. temperatureunder reflux for 8 hours
  2. customThe cooled reaction mixture
  3. filtrationis then filtered with suction
  4. washwashed with ethanol and ether
  5. customdried in air

Sources & evidence

ORD record
ord-ffa9307a1ea94722bc76b405569069ef
Source dataset
uspto-grants-2003_06
Patent number
US06576637B1

Reaction notes

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