Water → 2-[2,4-Difluoro-3-[[3-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetic acid

HRID 1771609Notes

Reaction equation

HRID 1771609 reaction equation
[F:1][C:2]1[C:14]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[CH:18]=2)=[C:13]([F:30])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8]CC)=[O:7].[OH-].[Na+].O>C1COCC1>[F:1][C:2]1[C:14]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[CH:18]=2)=[C:13]([F:30])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 89444317Ethyl 2-[2,4-difluoro-3-[[3-(3-fluorophenyl) phenyl]methylamino]phenoxy]acetate

Product 1

HCID 715155162-[2,4-Difluoro-3-[[3-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetic acidYield 75.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of intermediate ethyl 2-[2,4-difluoro-3-[[3-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetate (270 mg, 0.65 mmol, 1.0 eq) in THF (4 mL) was added NaOH (2 M aqueous solution, 2.5 mL, 5 mmol, 7.7 eq). The reaction was stirred at room temperature for 1 h. Water was added and the THF removed in vacuo. The aqueous layer was extracted with EtOAc and the combined organic extracts washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The crude material obtained was crystallised from CH2Cl2/petroleum ether, collected by filtration and dried in vacuo to give the title compound (I(e)) as a white solid (190 mg, 75%).

Workup

  1. customthe THF removed in vacuo
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic extracts washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude material obtained
  8. customwas crystallised from CH2Cl2/petroleum ether
  9. filtrationcollected by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-9d476766c261469595336250f77d033d
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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