Sodium Hydroxide → HCID 15840441, compound

HRID 2289296Notes

Reaction equation

HRID 2289296 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24]C)=[O:23])=[C:17]([O:26][CH2:27][C:28]([F:31])([F:30])[F:29])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([OH:24])=[O:23])=[C:17]([O:26][CH2:27][C:28]([F:31])([F:29])[F:30])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15840440HCID 15840440, compound

Product 1

HCID 15840441HCID 15840441, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 4-(N-tert-butyloxycarbonyl-4-piperidinyloxy)-2-(2,2,2-trifluoroethoxy)phenylacetate (3.0 g, MW=435, 6.90 mmol) from Step 7 above in MeOH (25 mL) was added a solution of aqueous NaOH (6.9 mL of a 2.0 N solution, 13.8 mmol). The mixture was refluxed for 3 h and then cooled to ambient temperature. The solvents were removed under reduced pressure and the residue was partitioned between EtOAc (100 mL) and 0.25 M aqueous citric acid (75 mL). The organic phase was separated and washed with H2O (25 mL) and brine (25 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. 4-(N-tert-butyloxycarbonyl-4-piperidinyloxy)-2-(2,2,2-trifluoroethoxy)phenylacetic acid was obtained as an amorphous solid (HPLC retention time=9.4 min (method A)).

Workup

  1. temperatureThe mixture was refluxed for 3 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 (75 mL)
  4. customThe organic phase was separated
  5. washwashed with H2O (25 mL) and brine (25 mL)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1e340412da684268bc2095ccb4ff5848
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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