Hydrochloric Acid → (S)-2-Amino-3-(4-(trifluoromethoxy)phenyl)propanoic acid hydrochloride

HRID 1799301Notes

Reaction equation

HRID 1799301 reaction equation
C([NH:4][C@@H:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=1)[C:6]([O:8]C)=[O:7])(=O)C.[ClH:22]>>[ClH:22].[NH2:4][C@@H:5]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18]([F:19])([F:20])[F:21])=[CH:15][CH:16]=1)[C:6]([OH:8])=[O:7]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 22950700Methyl (2s)-2-(acetylamino)-3-[4-(trifluoromethoxy)phenyl]propanoate

Product 1

HCID 69017088(S)-2-Amino-3-(4-(trifluoromethoxy)phenyl)propanoic acid hydrochlorideYield 93%

Conditions

Temperature
100 °C

Procedure

A 6 N hydrochloric acid (330 μL) solution of methyl (2S)-2-(acetylamino)-3-[4-(trifluoromethoxy)phenyl]propanoate (29.9 mg, 0.098 mmol) prepared in Reference Example 3 (3f) was stirred at 100° C. for 4 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The obtained residue was azeotroped with toluene, washed with diethyl ether, and dried under reduced pressure to give 26 mg of the title compound (white powder, yield: 93%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe obtained residue was azeotroped with toluene
  4. washwashed with diethyl ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-35acec976dbf4a369c114781f4a5801d
Source dataset
uspto-grants-2013_01
Patent number
US08344029B2

Reaction notes

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