Sodium Hydroxide → 4-[4-(Cyclopropanecarbonyl-amino)-cyclohexyloxy]-benzoic acid

HRID 555380Notes

Reaction equation

HRID 555380 reaction equation
C([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19]([CH:21]3[CH2:23][CH2:22]3)=[O:20])[CH2:14][CH2:13]2)=[CH:7][CH:6]=1)C.[OH-].[Na+]>CCO.C1COCC1.O>[CH:21]1([C:19]([NH:18][CH:15]2[CH2:14][CH2:13][CH:12]([O:11][C:8]3[CH:9]=[CH:10][C:5]([C:4]([OH:24])=[O:3])=[CH:6][CH:7]=3)[CH2:17][CH2:16]2)=[O:20])[CH2:23][CH2:22]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 666302994-[4-(Cyclopropanecarbonylamino)cyclohexyloxy]benzoic acid ethyl ester

Product 1

HCID 666293954-[4-(Cyclopropanecarbonyl-amino)-cyclohexyloxy]-benzoic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[4-(cyclopropanecarbonylamino)cyclohexyloxy]benzoic acid ethyl ester (4.75 g, 14.3 mmol) in EtOH (30 mL) and THF (10 mL) was added NaOH (2.29 g, 57.3 mmol) in 10 ml of water. Stirring was continued at ambient for 17 hrs. The solvents were removed under vacuum, water (50 mL) was added and the whole extracted with EtOAc. The aqueous layer was acidified to pH ˜2 with 2N HCl and the white precipitate obtained was filtered off and washed with hexane affording 4.0 g (92%) of 4-[4-(cyclopropanecarbonyl-amino)-cyclohexyloxy]-benzoic acid as a solid.

Workup

  1. customThe solvents were removed under vacuum, water (50 mL)
  2. additionwas added
  3. extractionthe whole extracted with EtOAc
  4. customthe white precipitate obtained
  5. filtrationwas filtered off
  6. washwashed with hexane affording 4.0 g (92%) of 4-[4-(cyclopropanecarbonyl-amino)-cyclohexyloxy]-benzoic acid as a solid

Sources & evidence

ORD record
ord-1d55ee6a014448cfaea2afffa60245d3
Source dataset
uspto-grants-2011_11
Patent number
US08053447B2

Reaction notes

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