Hydrochloric Acid → (7-Fluoro-4-methyl-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetic acid

HRID 591451Notes

Reaction equation

HRID 591451 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][C:5]1[C:9]2[C:10]([CH3:28])=[CH:11][C:12]([O:15][CH2:16][C:17]3[C:18]([CH3:27])=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=3)=[C:13]([F:14])[C:8]=2[S:7][CH:6]=1.C1COCC1.[OH-].[Na+].Cl>CO>[F:14][C:13]1[C:8]2[S:7][CH:6]=[C:5]([CH2:4][C:3]([OH:29])=[O:2])[C:9]=2[C:10]([CH3:28])=[CH:11][C:12]=1[O:15][CH2:16][C:17]1[C:18]([CH3:27])=[N:19][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 89775297Methyl(7-fluoro-4-methyl-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate

Product 1

HCID 89768174(7-Fluoro-4-methyl-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetic acidYield 86.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of methyl(7-fluoro-4-methyl-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate (159.8 mg), THF (dry) (2.0 mL) and MeOH (2.0 mL) was added 1N NaOH (1.122 mL) at room temperature. The mixture was stirred at room temperature for 2 h. The mixture was neutralized with 1N HCl and concentrated in vacuo. The precipitate was collected by filtration to give a solid. The solid was crystallized from EtOAc-hexane to give the title compound (134 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationThe precipitate was collected by filtration
  3. customto give a solid
  4. customThe solid was crystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-3d2abee50e6f4aba8842f12b0e34b3e7
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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