Sodium Hydroxide → 4-[[(1,1-Dimethylethoxy)carbonyl]amino]-2-(2,2,2-trifluoroethoxy)benzeneacetic acid

HRID 2289333Notes

Reaction equation

HRID 2289333 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18]C)=[O:17])=[C:11]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[C:11]([O:20][CH2:21][C:22]([F:23])([F:24])[F:25])[CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18700165HCID 18700165, compound

Product 1

HCID 543655024-[[(1,1-Dimethylethoxy)carbonyl]amino]-2-(2,2,2-trifluoroethoxy)benzeneacetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 4-(tert-butyloxycarbonylamino)-2-(2,2,2-trifluoroethoxy)phenylacetate (0.90 g, 2.5 mmol) in MeOH (15 mL) was added aqueous NaOH (2.5 mL of a 3 N solution, 7.5 mmol). The mixture was refluxed for 1 h. The solvents were removed under reduced pressure and the residue was partitioned between EtOAc (100 mL) and 0.25 M aqueous citric acid (25 mL). The organic phase was separated, washed with water (25 mL), dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give 4-(tert-butyloxycarbonylamino)-2-(2,2,2-trifluoroethoxy)-phenylacetic acid as an amorphous solid (HPLC retention time=8.8 min (method A)).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. customThe solvents were removed under reduced pressure
  3. customthe residue was partitioned between EtOAc (100 mL) and 0.25 M aqueous citric acid (25 mL)
  4. customThe organic phase was separated
  5. washwashed with water (25 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-bc22def30fb5461ca80d4943c34418e4
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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