Sodium Hydroxide → 2-[3-[[2Fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2,4-dimethyl-phenoxy]acetic acid

HRID 1771640Notes

Reaction equation

HRID 1771640 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[C:18]([CH3:31])=[C:19]([CH:27]=[CH:28][C:29]=1[CH3:30])[O:20][CH2:21][C:22]([O:24]CC)=[O:23].[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[C:18]([CH3:31])=[C:19]([CH:27]=[CH:28][C:29]=1[CH3:30])[O:20][CH2:21][C:22]([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89444191Ethyl 2-[3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate

Product 1

HCID 894438132-[3-[[2Fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2,4-dimethyl-phenoxy]acetic acidYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate (300 mg, 0.71 mmol, 1.0 eq) in THF (8 mL) was added a solution of NaOH (1M aqueous solution, 3 mL, 3 mmol, 4.2 eq) at room temperature. The reaction mixture was stirred 1 h, then the THF was removed in vacuo. The remaining aqueous solution was poured into water and adjusted to pH 3 by addition of 1M HCl. The solid precipitate that formed was collected by filtration, washed with water and dried in vacuo to give the title compound (I(j)) as a solid (250 mg, 89%).

Workup

  1. customthe THF was removed in vacuo
  2. additionThe remaining aqueous solution was poured into water
  3. additionadjusted to pH 3 by addition of 1M HCl
  4. customThe solid precipitate that formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-c046b749aa91466b82324870a19fe611
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

Loading…