Sodium Hydroxide → (3-{3-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]-1,2,4-oxadiazol-5-yl}-1H-pyrrol-1-yl)acetic acid

HRID 561217Notes

Reaction equation

HRID 561217 reaction equation
[Br:1][C:2]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:15]=[C:14]([C:16]3[CH:20]=[CH:19][N:18]([CH2:21][C:22]([O:24]CC)=[O:23])[CH:17]=3)[O:13][N:12]=2)[CH2:7][CH2:6]1.[OH-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:15]=[C:14]([C:16]3[CH:20]=[CH:19][N:18]([CH2:21][C:22]([OH:24])=[O:23])[CH:17]=3)[O:13][N:12]=2)[CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86620461Ethyl (3-{3-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]-1,2,4-oxadiazol-5-yl}-1H-pyrrol-1-yl)acetate

Product 1

HCID 57518493(3-{3-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]-1,2,4-oxadiazol-5-yl}-1H-pyrrol-1-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (3-{3-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]-1,2,4-oxadiazol-5-yl}-1H-pyrrol-1-yl)acetate (35 mg, 0.071 mmol) in THF (236 μL) and MeOH (118 μL) was added 1N NaOH (142 μL, 0.142 mmol). The mixture was stirred at RT for 10 min. The THF and MeOH were removed by evaporation under diminished pressure and the aqueous layer was washed with Et2O (2×2 mL). The aqueous layer was acidified to pH 1 with 1N HCl and extracted with EtOAc (3×2 mL). The combined organic fractions were dried over Na2SO4 and the solvent was evaporated to afford the title compound.

Workup

  1. customThe THF and MeOH were removed by evaporation under diminished pressure
  2. washthe aqueous layer was washed with Et2O (2×2 mL)
  3. extractionextracted with EtOAc (3×2 mL)
  4. dry with materialThe combined organic fractions were dried over Na2SO4
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4ddb5eb1c0ee444d9278c8c3b9195f63
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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