Hydrochloric Acid → Butanoic acid, 2-amino-4,4-difluoro-, hydrochloride (1:1)

HRID 19323Notes

Reaction equation

HRID 19323 reaction equation
C([O:3][C:4](=[O:19])[C:5]([NH:15]C(=O)C)([CH2:11][CH:12]([F:14])[F:13])C(OCC)=O)C.[ClH:20]>>[ClH:20].[NH2:15][CH:5]([CH2:11][CH:12]([F:14])[F:13])[C:4]([OH:19])=[O:3]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 17749984Diethyl 2-acetamido-2-(2,2-difluoroethyl)malonate

Product 1

HCID 47003332Butanoic acid, 2-amino-4,4-difluoro-, hydrochloride (1:1)Yield 97%

Procedure

In a flask was placed 2-acetylamino-2-(2,2-difluoro-ethyl)-malonic acid diethyl ester (8.94 g, 31.78 mmol) and 6N aqueous hydrochloric acid (140 mL). This mixture was refluxed overnight. After this time, the mixture was cooled to room temperature and extracted with diethyl ether (100 mL) the aqueous layer was concentrated in vacuo, azeotroped with acetonitrile and dried under high vacuum to afford 2-amino-4,4-difluoro-butyric acid hydrochloride salt (5.39 g, 97%) as a cream colored solid.

Workup

  1. customIn a flask was placed
  2. temperatureThis mixture was refluxed overnight
  3. extractionextracted with diethyl ether (100 mL) the aqueous layer
  4. concentrationwas concentrated in vacuo
  5. customazeotroped with acetonitrile
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-c9fda19b50b74a45a68557364533658c
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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