Hydrochloric Acid → Benzenepropanoic acid, b-aMino-, hydrochloride

HRID 132067Notes

Reaction equation

HRID 132067 reaction equation
C([NH:4][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8])(=O)C.[ClH:16]>Cl.CO>[ClH:16].[NH2:4][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 34808823-Acetamido-3-phenylpropanoic acid

Product 1

HCID 2868374Benzenepropanoic acid, b-aMino-, hydrochlorideYield 39.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

(+)-3-acetylamino-3-phenylpropanoic acid (207 mg, 1.00 mmol) prepared by the same manner as in Example 3 and 2.0 ml of 2M hydrochloric acid were added to a 30-ml two-necked flask equipped with a stirrer and heated to reflux for 3 hours. After 3 hours, 1 drop of concentrated hydrochloric acid was added to the reaction solution using a Pasteur pipette and the mixture was heated to reflux for 2 hours more. After completion of the reaction, the reaction solution was evaporated to dryness in vacuo, and the resulting residue was washed with a mixed solvent of methanol/diisopropyl and recrystallized from a mixed solvent of 2-propanol/99% ethanol to give 79 mg (0.392 mmol) of (+)-3-amino-3-phenylpropanoic acid hydrochloride in a yield of 39.2% (melting point: 195 to 196° C., [α]D=−3.03° (c=1.0, methanol)).

Workup

  1. additionwere added to a 30-ml two-necked flask
  2. customequipped with a stirrer
  3. temperatureheated
  4. temperatureto reflux for 3 hours
  5. temperaturethe mixture was heated
  6. temperatureto reflux for 2 hours more
  7. customAfter completion of the reaction
  8. customthe reaction solution was evaporated to dryness in vacuo
  9. washthe resulting residue was washed with a mixed solvent of methanol/diisopropyl
  10. customrecrystallized from a mixed solvent of 2-propanol/99% ethanol

Sources & evidence

ORD record
ord-4dece94296074b54b664fb89f3652df6
Source dataset
uspto-grants-2008_06
Patent number
US07385080B2

Reaction notes

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