Ammonia → (2S)-2-amino-2-phenylpropanoic acid

HRID 613769Notes

Reaction equation

HRID 613769 reaction equation
[CH3:1][C@@:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:6]C(=O)N[C:3]1=[O:8].[OH2:15].N>C(OCC)(=O)C>[NH2:6][C@:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:1])[C:3]([OH:15])=[O:8]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 640021(5S)-5-methyl-5-phenylimidazolidine-2,4-dione

Product 1

HCID 853461(2S)-2-amino-2-phenylpropanoic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

22 g (0.115 mol) of (+)-(5S)-5-methyl-5-phenylhydantoin, 100 ml of water and 100 ml of 28% aqueous ammonia are introduced successively into a 1 liter autoclave. The medium is heated at 160° C. for 15 hours. After cooling to room temperature, the solution is concentrated under reduced pressure. The white solid obtained is treated with 100 ml of ethyl acetate for 2 hours and then filtered and dried under vacuum at 80° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe solution is concentrated under reduced pressure
  3. customThe white solid obtained
  4. filtrationfiltered
  5. customdried under vacuum at 80° C.

Sources & evidence

ORD record
ord-64ea23b555f84b6cb5af51491a97a742
Source dataset
uspto-grants-1999_12
Patent number
US06008370

Reaction notes

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