Hydrochloric Acid → ({4-[(2-(Ethyloxy)-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}ethyl)thio]-2-methylphenyl}oxy)acetic acid

HRID 1391822Notes

Reaction equation

HRID 1391822 reaction equation
[CH2:1]([O:3][CH2:4][CH:5]([S:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]([O:33]CC)=[O:32])=[C:25]([CH3:36])[CH:24]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[N:7]=1)[CH3:2].[OH-].[Na+].Cl>C1COCC1.CO>[CH2:1]([O:3][CH2:4][CH:5]([S:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]([OH:33])=[O:32])=[C:25]([CH3:36])[CH:24]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:16][CH:17]=2)[N:7]=1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58629824Ethyl ({4-[(2-(ethyloxy)-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}ethyl)thio]-2-methylphenyl}oxy)acetate

Product 1

HCID 10097139({4-[(2-(Ethyloxy)-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}ethyl)thio]-2-methylphenyl}oxy)acetic acidYield 61.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the ethyl ({4-[(2-(ethyloxy)-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}ethyl)thio]-2-methylphenyl}oxy)acetate (Enantiomer 1) (12 mg, 0.023 mmol) in THF (1 mL) and MeOH (1 mL) was treated with aqueous NaOH (2N, 1 mL) and the resulting mixture agitated at ambient temperature for 15 h. Aqueous HCl (2N, 1 mL) was then added and the organic solvents removed under vacuum using a Genevac. The residue was the then made up to 2 mL by the addition of water and then extracted using DCM (3×3 mL) in an hydrophobic frit. The residue was reduced and then purified further by mass directed autoprep HPLC to afford the title compound as an oil (7 mg).

Workup

  1. customthe organic solvents removed under vacuum
  2. additionthen made up to 2 mL by the addition of water
  3. extractionextracted
  4. custompurified further by mass

Sources & evidence

ORD record
ord-be7d6bcf6da24a43a85f72efa4072bec
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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