Malonic Acid → (r)-3-(p-Bromophenyl)-beta-alanine

HRID 898094Notes

Reaction equation

HRID 898094 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([O-:13])(=[O:12])[CH3:11].[NH4+:14].C(O)(=O)CC(O)=O>C(O)C.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C@@H:6]([CH2:11][C:10]([OH:13])=[O:12])[NH2:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 707414-BromobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 724054(r)-3-(p-Bromophenyl)-beta-alanineYield 63%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

p-Bromo-benzaldehyde (10.0 g, 54 mmol) was mixed with 100 ml of ethanol/water (95/5), 8.3 g of ammonium acetate (108 mmol), and 11.2 g of malonic acid (108 mmol), heated under reflux at 80° C. with stirring for 17 hours, filtered under heating and dried under reduced pressure to give 8.3 g of p-bromo-β-phenylalanine crystals at a yield of 62.8%.

Workup

  1. temperatureheated
  2. filtrationfiltered
  3. temperatureunder heating
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-50675645573b4d7ea63ad236cf72995d
Source dataset
uspto-grants-2008_04
Patent number
US07351571B2

Reaction notes

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