Methanol → (4-Methyl-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetic acid

HRID 591401Notes

Reaction equation

HRID 591401 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][C:5]1[C:9]2[C:10]([CH3:26])=[CH:11][C:12]([O:14][CH2:15][C:16]3[N:20]([CH3:21])[N:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)=[CH:13][C:8]=2[S:7][CH:6]=1.CO.[OH-].[Na+]>C1COCC1>[CH3:26][C:10]1[C:9]2[C:5]([CH2:4][C:3]([OH:27])=[O:2])=[CH:6][S:7][C:8]=2[CH:13]=[C:12]([O:14][CH2:15][C:16]2[N:20]([CH3:21])[N:19]=[C:18]([C:22]([F:25])([F:23])[F:24])[CH:17]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 89775282Methyl(4-methyl-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetate

Product 1

HCID 89768820(4-Methyl-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetic acidYield 91.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl(4-methyl-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetate (132.1 mg), MeOH (2.0 mL) and THF (dry) (2.0 mL) was added 1N NaOH (0.663 mL). The mixture was stirred at room temperature for 2 h. The mixture was concentrated. The mixture was neutralized with 1N HCl and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was crystallized from EtOAc-hexane to give the title compound (117 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-9d638b3f2b724f12abd0f8f8acbf317d
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

Loading…