Acetic Acid → (3R)-3-Amino-3-(4-nitrophenyl)propanoic acid

HRID 898096Notes

Reaction equation

HRID 898096 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].C([O-])(=O)C.[NH4+:9].[N+:10]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1)([O-:12])=[O:11].C(O)(=O)CC(O)=O>CC(O)C>[N+:10]([C:13]1[CH:20]=[CH:19][C:16]([C@@H:17]([CH2:2][C:1]([OH:4])=[O:3])[NH2:9])=[CH:15][CH:14]=1)([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5414-NitrobenzaldehydeHCID 867Malonic AcidHCID 517165Ammonium Acetate2×

Product 1

HCID 1381949(3R)-3-Amino-3-(4-nitrophenyl)propanoic acidYield 52%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

Acetic acid (110 ml) was mixed with 20.4 g of ammonium acetate (264 mmol) and heated to 85° C. After ammonium acetate was dissolved, the mixture was further mixed with 20.0 g of p-nitro-benzaldehyde (132 mmol) and 27.8 g of malonic acid (264 mmol) and heated at 90° C. with stirring for 5 hours. After being cooled to room temperature, the filtrate was mixed with 300 ml of 2-propanol. The precipitated crystal was filtered, subjected to slurry washing with 100 ml of ethanol, filtered again and dried under reduced pressure to give 14.4 g of p-nitro-β-phenylalanine at a yield of 52.0%.

Workup

  1. temperatureheated at 90° C.
  2. temperatureAfter being cooled to room temperature
  3. filtrationThe precipitated crystal was filtered
  4. washto slurry washing with 100 ml of ethanol
  5. filtrationfiltered again
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-a527c186e6e543a2ae93c96fe96c45dd
Source dataset
uspto-grants-2008_04
Patent number
US07351571B2

Reaction notes

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