Sodium Hydroxide → 2-[2,4-Difluoro-3-[[6-fluoro-3-(3-fluorophenyl)-2-methyl-phenyl]methylamino]phenoxy]acetic acid

HRID 1771724Notes

Reaction equation

HRID 1771724 reaction equation
[F:1][C:2]1[C:14]([NH:15][CH2:16][C:17]2[C:22]([F:23])=[CH:21][CH:20]=[C:19]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=3)[C:18]=2[CH3:31])=[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.CO>[F:1][C:2]1[C:14]([NH:15][CH2:16][C:17]2[C:22]([F:23])=[CH:21][CH:20]=[C:19]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=3)[C:18]=2[CH3:31])=[C:13]([F:32])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 89444025Ethyl 2-[2,4-difluoro-3-[[6-fluoro-3-(3-fluorophenyl)-2-methyl-phenyl]methylamino]phenoxy]acetate

Product 1

HCID 894440722-[2,4-Difluoro-3-[[6-fluoro-3-(3-fluorophenyl)-2-methyl-phenyl]methylamino]phenoxy]acetic acidYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[2,4-difluoro-3-[[6-fluoro-3-(3-fluorophenyl)-2-methyl-phenyl]methylamino]phenoxy]acetate (240 mg, 0.53 mmol, 1.0 eq) in a mixture of THF (2 mL) and MeOH (2 mL) was added NaOH (2M aqueous solution, 2 mL, 4.0 mmol). The reaction mixture was stirred at room temperature for 3 h. The THF and MeOH were evaporated in vacuo and the pH of the aqueous phase adjusted to pH 3 by addition of diluted HCl. The solid that formed was collected by filtration, washed with water and dried to give the title compound as a white solid (150 mg, 68%).

Workup

  1. customThe THF and MeOH were evaporated in vacuo
  2. additionthe pH of the aqueous phase adjusted to pH 3 by addition of diluted HCl
  3. customThe solid that formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-fb433164fd6d4bceaaee3b5c54886fe2
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

Loading…