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

HRID 1771626Notes

Reaction equation

HRID 1771626 reaction equation
[F:1][C:2]1[C:14]([NH:15][CH2:16][C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[CH:20]=[C:19]([CH3:30])[C:18]=2[F:31])=[C:13]([F:32])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8]CC)=[O:7].[OH-].[Na+]>C1COCC1>[F:1][C:2]1[C:14]([NH:15][CH2:16][C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[CH:20]=[C:19]([CH3:30])[C:18]=2[F:31])=[C:13]([F:32])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89443610Ethyl 2-[2,4-difluoro-3-[[2-fluoro-5-(3-fluorophenyl)-3-methyl-phenyl]methylamino]phenoxy]acetate

Product 1

HCID 894437002-[2,4-Difluoro-3-[[2-fluoro-5-(3-fluorophenyl)-3-methyl-phenyl]methylamino]phenoxy]acetic acidYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 2-[2,4-difluoro-3-[[2-fluoro-5-(3-fluorophenyl)-3-methyl-phenyl]methylamino]phenoxy]acetate (150 mg, 0.34 mmol, 1.0 eq) in THF (8 mL) was added NaOH (1M in water, 3.0 mL, 3.0 mmol) at room temperature. The reaction was stirred for 2 h, then the THF was removed in vacuo and the aqueous layer acidified to pH 4 by addition of 1M HCl. The resultant precipitate was collected by filtration and dried in vacuo to give the title compound (I(h)) (120 mg, 85%) as a white solid.

Workup

  1. customthe THF was removed in vacuo
  2. additionthe aqueous layer acidified to pH 4 by addition of 1M HCl
  3. filtrationThe resultant precipitate was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-25d0d92e55a14325a2167c1fcd7319f1
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

Loading…