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

HRID 1771630Notes

Reaction equation

HRID 1771630 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]=[CH:19][C:18]=2[F:30])=[C:13]([CH3:31])[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]=[CH:19][C:18]=2[F:30])=[C:13]([CH3:31])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89443509Ethyl 2-[2-fluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-4-methyl-phenoxy]acetate

Product 1

HCID 894440292-[2-Fluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-4-methyl-phenoxy]acetic acidYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[2-fluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-4-methyl-phenoxy]acetate (260 mg, 0.61 mmol, 1.0 eq) in THF (10 mL) was added NaOH (1M aqueous solution, 5 mL, 5 mmol, 8.2 eq) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 1 h. The organic solvent was evaporated in vacuo and the mixture that remained poured into water. The pH was adjusted to pH 4-6 with dilute HCl and the precipitate that formed was collected by filtration, washed with water and dried in vacuo to give title compound (I(i)) as a solid (200 mg, 82%).

Workup

  1. customThe organic solvent was evaporated in vacuo
  2. additionthe mixture that remained poured into water
  3. customthe precipitate that formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-5e89d65e17bc41bdb651c069dfc9ea5d
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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