Hydrochloric Acid → HCID 67111333, compound

HRID 540795Notes

Reaction equation

HRID 540795 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:38]=[CH:37][C:6]([O:7][C:8]2[N:12]([CH2:13][C:14]([O:16]CC)=[O:15])[N:11]=[C:10]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]4([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:28][O:27][CH2:26]4)[CH:20]=3)[CH:9]=2)=[CH:5][CH:4]=1.[OH-].[Na+].Cl>CCO>[F:40][C:2]([F:1])([F:39])[C:3]1[CH:38]=[CH:37][C:6]([O:7][C:8]2[N:12]([CH2:13][C:14]([OH:16])=[O:15])[N:11]=[C:10]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]4([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:34])[CH3:35])=[O:31])[CH2:26][O:27][CH2:28]4)[CH:20]=3)[CH:9]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71274761HCID 71274761, compound

Product 1

HCID 67111333HCID 67111333, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl [5-(4-trifluoromethylphenoxy)-3-(3-{3-[(tert-butyloxycarbonyl)amino]oxetan-3-yl}phenyl)-1H-pyrazol-1-yl]acetate (98 mg, 0.18 mmol) was dissolved in 0.5 mL of EtOH and to the stirred solution was added 1N aqueous NaOH solution (0.35 mL, 0.35 mmol). The mixture was stirred for 20 min and then 0.35 mL of 1N aqueous HCl was added dropwise. The solvents were removed under reduced pressure and the residue was partitioned between EtOAc and 10% aqueous citric acid solution. The organic phase was washed with brine, dried over MgSO4, filtered, and the solvent was removed under reduced pressure to give [5-(4-trifluoromethylphenoxy)-3-(3-{3-[(tert-butyloxycarbonyl)amino]oxetan-3-yl}phenyl)-1H-pyrazol-1-yl]acetic acid as a foam. Calcd (M+1)+: 534.5. Found: 534.8

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and 10% aqueous citric acid solution
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-06cb3899998147bb9907da1267034e27
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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