Hydrochloric Acid → 3-Amino-2,2-difluoropentanoic acid

HRID 238755Notes

Reaction equation

HRID 238755 reaction equation
C([N:8](CC1C=CC=CC=1)[CH2:9][C:10]([F:17])([F:16])[C:11]([O:13]CC)=[O:12])C1C=CC=CC=1.Cl.[CH3:26][CH2:27]O>[OH-].[OH-].[Pd+2]>[CH2:26]([CH:9]([NH2:8])[C:10]([F:16])([F:17])[C:11]([OH:13])=[O:12])[CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 11256065Ethyl 3-(dibenzylamino)-2,2-difluoropropanoate

Product 1

HCID 866130473-Amino-2,2-difluoropentanoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

To a solution of ethyl 3-(dibenzylamino)-2,2-difluoropropanoate (517 mg, 1.55 mmol) in EtOH (1 mL) was added 0.5 N HCl (1 mL) and Pd(OH)2/C (20%, 50 mg). The reaction mixture was stirred at room temperature under H2 atmosphere for 3 days. The reaction mixture was filtered and the solid was rinsed with water and ether. The aqueous layer was separated from the ether layer and lyophilized to yield ethyl 3-amino-2,2-difluoropropanoic acid as a white solid (210 mg, 100% yield). 1H NMR (400 MHz, DMSO) ppm 3.27-3.46 (m, 2H), 8.06-8.64 (m, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was rinsed with water and ether
  3. customThe aqueous layer was separated from the ether layer

Sources & evidence

ORD record
ord-f4c0eaa4e9924ff7bef9426d07363251
Source dataset
uspto-grants-2014_02
Patent number
US08642576B2

Reaction notes

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