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

HRID 1771599Notes

Reaction equation

HRID 1771599 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[CH3:30])=[C:13]([F: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[CH3:30])=[C:13]([F: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 89444115Ethyl 2-[2,4-difluoro-3-[[5-(3-fluorophenyl)-2-methyl-phenyl]methylamino]phenoxy]acetate

Product 1

HCID 715164492-[2,4-Difluoro-3-[[5-(3-fluorophenyl)-2-methyl-phenyl]methylamino]phenoxy]acetic acidYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 2-[2,4-difluoro-3-[[5-(3-fluorophenyl)-2-methyl-phenyl]methylamino]phenoxy]acetate (100 mg, 0.23 mmol, 1.0 eq) in THF (8 mL) was added NaOH (1M aqueous solution, 3 mL, 3 mmol, 13.0 eq) at room temperature. The reaction was stirred at room temperature for 2 h. The THF was evaporated in vacuo and the aqueous layer acidified to pH 3 by addition of 1M HCl. The resultant precipitate was collected by filtration and dried in vacuo to give the title compound (I(c)) as a white solid (85 mg, 91%).

Workup

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

Sources & evidence

ORD record
ord-76ef1173b5904f458635eaf40a722f37
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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