Water → HCID 18700106, compound

HRID 2289307Notes

Reaction equation

HRID 2289307 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:22]=[CH:21][C:18]([C:19]#N)=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:27].[Na+].[OH2:29]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:22]=[CH:21][C:18]([C:19]([OH:29])=[O:27])=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 18700146HCID 18700146, compound

Product 1

HCID 18700106HCID 18700106, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 4-(N-tert-butyloxy-carbonyl-4-piperidinyloxy)-2-trifluoromethylbenzonitrile (1.5 g, 3.7 mmol) from Step 1 above in EtOH (25 mL) was added aqueous NaOH (2.3 g, 57 mmol in 15 mL of water). The mixture was heated to reflux for 48 h. Water was added (50 mL) and the volume was concentrated under reduced pressure to ~50 mL. The mixture was extracted with CH2Cl2 (2×25 mL) and the aqueous phase was acidified to pH 3 by the addition of 5 N aqueous HCl. The mixture was extracted with CH2Cl2 (3×25 mL) and the combined organic extracts were dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give 4-(N-tert-butyloxycarbonyl-4-piperidinyloxy)-2-trifluoromethylbenzoic acid as an amorphous solid (HPLC retention time=10.0 min (method A)).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 48 h
  3. concentrationthe volume was concentrated under reduced pressure to ~50 mL
  4. extractionThe mixture was extracted with CH2Cl2 (2×25 mL)
  5. additionthe aqueous phase was acidified to pH 3 by the addition of 5 N aqueous HCl
  6. extractionThe mixture was extracted with CH2Cl2 (3×25 mL)
  7. dry with materialthe combined organic extracts were dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-03447c17a09147ee8d64e4d3fbfe76e9
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

Loading…