Hydrochloric Acid → HCID 10048485, compound

HRID 1391805Notes

Reaction equation

HRID 1391805 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[N:11]=2)[CH:5]=[CH:4][C:3]=1[O:26][CH2:27][C:28]([O:30]CC)=[O:29].[OH-].[Na+].Cl.CCOC(C)=O>C1COCC1>[CH3:1][C:2]1[CH:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:18][CH:17]=3)[N:11]=2)[CH:5]=[CH:4][C:3]=1[O:26][CH2:27][C:28]([OH:30])=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 58629944HCID 58629944, compound

Product 1

HCID 10048485HCID 10048485, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl ({2-methyl-4-[({6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}methyl)thio]phenyl}oxy)acetate (367 mg, 0.80 mmol) in THF (5 mL) was treated with aqueous NaOH (2M, 5 mL) and the resulting solution stirred at rt for 4 hours. The mixture was poured into a mixture of aqueous HCl (2M) and EtOAc and the layers separated. The organic layer was then washed with water and brine, dried MgSO4, filtered and then reduced under vacuum. Purification by mass-directed auto-prep HPLC afforded the title compound as an oil.

Workup

  1. customthe layers separated
  2. washThe organic layer was then washed with water and brine, dried MgSO4
  3. filtrationfiltered
  4. customPurification by mass-directed auto-prep HPLC

Sources & evidence

ORD record
ord-75d37a010b784f959baeb0ee4dab96e5
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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