Tetrahydrofuran → 3-Benzyloxycarbonylamino-2,2-difluoropropionic acid

HRID 2415645Notes

Reaction equation

HRID 2415645 reaction equation
C[O:2][C:3](=[O:19])[C:4]([F:18])([F:17])[CH2:5][NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].C1COCC1.[OH-].[Na+]>CO>[CH2:10]([O:9][C:7]([NH:6][CH2:5][C:4]([F:17])([F:18])[C:3]([OH:19])=[O:2])=[O:8])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 235267113-Benzyloxycarbonylamino-2,2-difluoropropionic acid methyl ester

Product 1

HCID 226353073-Benzyloxycarbonylamino-2,2-difluoropropionic acidYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Benzyloxycarbonylamino-2,2-difluoropropionic acid methyl ester (3.3 g, 12.1 mmol), THF (50 ml), methanol (50 ml) and 1 N sodium hydroxide solution (50ml) were mixed and stirred for 16 hours at room temperature. After adjusting the pH to acidic reaction and removal of organic solvent by evaporation, the aqueous residue was extracted twice with ethyl acetate. The combined organic layers were washed twice with 5% brine, dried over magnesium sulphate and filtered through a short silica column before concentration in vacuo to afford 2.6 g (83%) of 3-benzyloxycarbonylamino-2,2-difluoropropionic acid as an oil.

Workup

  1. customto acidic reaction and removal of organic solvent
  2. customby evaporation
  3. extractionthe aqueous residue was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed twice with 5% brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered through a short silica column before concentration in vacuo

Sources & evidence

ORD record
ord-c88b25d4c7b74ea691ee76bf8da6acd5
Source dataset
uspto-grants-2004_11
Patent number
US06821960B2

Reaction notes

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