Sodium Hydroxide → HCID 18700161, compound

HRID 2289313Notes

Reaction equation

HRID 2289313 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:34])([F:33])[C:29]([F:32])([F:31])[F:30])[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:34])([F:33])[C:29]([F:30])([F:31])[F:32])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18700136HCID 18700136, compound

Product 1

HCID 18700161HCID 18700161, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 4-(N-tert-butyloxycarbonyl-4-piperidinyloxy)-2-(2,2,3,3,3-pentafluoropropyloxy)phenylacetate (0.40 g, 0.82 mmol) from Step 2 above in MeOH (5 mL) was added a solution of aqueous NaOH (0.82 mL of a 2.0 N solution, 1.6 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 (50 mL) and 0.25 M aqueous citric acid (25 mL). The organic phase was separated and washed with H2O (10 mL) and brine (10 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. 4-(N-tert-Butyloxycarbonyl-4-piperidinyloxy)-2-(2,2,3,3,3-pentafluoropropyloxy)phenylacetic acid was obtained as an amorphous solid (HPLC retention time=9.7 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 (50 mL) and 0.25 M aqueous citric acid (25 mL)
  4. customThe organic phase was separated
  5. washwashed with H2O (10 mL) and brine (10 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-054bf259db524eb8b7ac38f08863876d
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

Loading…