Hydrochloric Acid → (4-Fluoro-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetic acid

HRID 591566Notes

Reaction equation

HRID 591566 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][C:5]1[C:9]2[C:10]([F:27])=[CH:11][C:12]([O:14][CH2:15][C:16]3[C:17]([CH3:26])=[N:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=3)=[CH:13][C:8]=2[S:7][CH:6]=1.[OH-].[Na+].C1COCC1.Cl>O.CO>[F:27][C:10]1[C:9]2[C:5]([CH2:4][C:3]([OH:28])=[O:2])=[CH:6][S:7][C:8]=2[CH:13]=[C:12]([O:14][CH2:15][C:16]2[C:17]([CH3:26])=[N:18][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:20][CH:21]=2)[CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 118667067Methyl(4-fluoro-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate

Product 1

HCID 89767876(4-Fluoro-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetic acidYield 90.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl(4-fluoro-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate (240 mg), 1N NaOH (2 mL), THF (2 mL) and MeOH (2 mL) was stirred at room temperature for 1.5 h. To the mixture were added 1N HCl (2 mL) and water. The mixture was extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residual solid was washed with hexane to give the title compound (210 mg). The crystals were crystallized from acetone-hexane.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. washThe residual solid was washed with hexane

Sources & evidence

ORD record
ord-641966388bd640cd81bc36ef502974b8
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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