Sodium Hydroxide → 2-[4-Chloro-2-fluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetic acid

HRID 1771644Notes

Reaction equation

HRID 1771644 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10]CC)=[O:9])=[C:4]([F:15])[C:3]=1[NH:16][CH2:17][C:18]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[CH:21]=[CH:20][C:19]=1[F:31].[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[C:4]([F:15])[C:3]=1[NH:16][CH2:17][C:18]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[CH:21]=[CH:20][C:19]=1[F:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89443532Ethyl 2-[4-chloro-2-fluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetate

Product 1

HCID 894437362-[4-Chloro-2-fluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetic acidYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 2-[4-chloro-2-fluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetate (80 mg, 0.18 mmol, 1.0 eq) in THF (6 mL) was added to a 1M solution of NaOH (2 mL, 2 mmol, 11.1 eq). The reaction mixture was stirred at room temperature for 2 h. The organic solvent was removed in vacuo and the aqueous solution diluted with water. The solution was adjusted to pH 3 by addition of diluted HCl and the precipitate that formed collected by filtration, washed with water and dried in vacuo to give the title compound (I(k)) as white solid (65 mg, 87%).

Workup

  1. customThe organic solvent was removed in vacuo
  2. additionthe aqueous solution diluted with water
  3. additionThe solution was adjusted to pH 3 by addition of diluted HCl
  4. customthe precipitate that formed
  5. filtrationcollected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-56722823ad214d9e80fc84bfea20d589
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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