HCID 58629829, compound → HCID 10094335, compound

HRID 1391803Notes

Reaction equation

HRID 1391803 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([S:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[O:26][CH2:27][C:28]([O:30]CC)=[O:29]>C1COCC1.[OH-].[Na+]>[CH3:1][C:2]1[CH:7]=[C:6]([S:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:18][CH:17]=3)[CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[O:26][CH2:27][C:28]([OH:30])=[O:29]

Participants

4

Reactant 1

HCID 58629829HCID 58629829, compound

Product 1

HCID 10094335HCID 10094335, compoundYield 12.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of ethyl {[2-methyl-4-({[4′-(trifluoromethyl)-3-biphenylyl]methyl}thio)phenyl]oxy}acetate (209 mg) in THF (20 mL) and aqueous NaOH (2M, 20 mL) was stirred at rt overnight and then heated to 60° C. for 2 hours. The mixture was then allowed to cool to rt and the THF removed under vacuum. The resulting aqueous mixture was then acidified and extracted with EtOAc (3×) and the organic layer washed with brine dried (MgSO4), filtered and reduced. Purification by mass directed auto-prep HPLC afforded the title compound as a white solid (24 mg).

Workup

  1. temperatureto cool to rt
  2. customthe THF removed under vacuum
  3. extractionextracted with EtOAc (3×)
  4. washthe organic layer washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customPurification by mass

Sources & evidence

ORD record
ord-5efc182f9ae945648216ab320e266069
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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