Potassium Carbonate → 4-(Cyclopropylmethoxy)-N-{(1S)-2-[(2-hydroxyethyl)amino]-2-oxo-1-[4-(trifluoromethoxy)benzyl]ethyl}benzamide

HRID 1799268Notes

Reaction equation

HRID 1799268 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][CH2:12][NH:13][C:14](=[O:42])[C@@H:15]([NH:28][C:29](=[O:41])[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH:38]2[CH2:40][CH2:39]2)=[CH:32][CH:31]=1)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1)(=O)C>CO>[CH:38]1([CH2:37][O:36][C:33]2[CH:34]=[CH:35][C:30]([C:29]([NH:28][C@@H:15]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=3)[C:14]([NH:13][CH2:12][CH2:11][OH:10])=[O:42])=[O:41])=[CH:31][CH:32]=2)[CH2:40][CH2:39]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 690173752-({(2S)-2-{[4-(Cyclopropylmethoxy)benzoyl]amino}-3-[4-(trifluoromethoxy)phenyl]propanoyl}amino)ethyl acetate

Product 1

HCID 690192294-(Cyclopropylmethoxy)-N-{(1S)-2-[(2-hydroxyethyl)amino]-2-oxo-1-[4-(trifluoromethoxy)benzyl]ethyl}benzamideYield 54.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (32 mg, 0.23 mmol) was added at room temperature to a methanol (230 mL) suspension of 2-({(2S)-2-{[4-(cyclopropylmethoxy)benzoyl]amino}-3-[4-(trifluoromethoxy)phenyl]propanoyl}amino)ethyl acetate (1.17 g, 2.30 mmol) prepared in Example 50. The mixture was stirred for 1.5 hours, and then the reaction solution was evaporated. To the obtained residue was added ethyl acetate (200 mL). The mixture was washed with a saturated ammonium chloride aqueous solution (200 mL) and saturated brine and was dried over anhydrous sodium sulfate. The solvent was evaporated to give a crude crystalline solid, which was recrystallized with ethyl acetate (20 mL) to give 582 mg of the title compound (white powder, yield: 54%).

Workup

  1. customthe reaction solution was evaporated
  2. additionTo the obtained residue was added ethyl acetate (200 mL)
  3. washThe mixture was washed with a saturated ammonium chloride aqueous solution (200 mL) and saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customto give a crude crystalline solid, which
  7. customwas recrystallized with ethyl acetate (20 mL)

Sources & evidence

ORD record
ord-e5962d2cab42436a863f3e918e97d4e1
Source dataset
uspto-grants-2013_01
Patent number
US08344029B2

Reaction notes

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