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

HRID 1771676Notes

Reaction equation

HRID 1771676 reaction equation
[F:1][C:2]1[C:14]([NH:15][CH2:16][C:17]2[CH:22]=[C:21]([OH:23])[CH:20]=[C:19]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=3)[CH:18]=2)=[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]([OH:23])[CH:20]=[C:19]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=3)[CH:18]=2)=[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 89444233Ethyl 2-[2,4-difluoro-3-[[3-(3-fluorophenyl)-5-hydroxy-phenyl]methylamino]phenoxy]acetate

Product 1

HCID 894441262-[2,4-Difluoro-3-[[3-(3-fluorophenyl)-5-hydroxy-phenyl]methylamino]phenoxy]acetic acidYield 91.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[2,4-difluoro-3-[[3-(3-fluorophenyl)-5-hydroxy-phenyl]methylamino]phenoxy]acetate (II(b)) (200 mg, 0.46 mmol, 1.0 eq) in THF (10 mL) was added NaOH (1M, 6 mL, 6 mmol, 13.0 eq) at 0° C. The reaction mixture was allowed to warm room temperature and was stirred for 3 h. The THF was removed in vacuo and the remaining solution diluted with water and adjusted to pH 4-6 by addition of diluted HCl. The precipitate that formed was collected by filtration and dried in vacuo to give the title compound (I(p)) as a solid (170 mg, 91%).

Workup

  1. customThe THF was removed in vacuo
  2. additionthe remaining solution diluted with water
  3. additionadjusted to pH 4-6 by addition of diluted HCl
  4. customThe precipitate that formed
  5. filtrationwas collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-7d62999d8684462ab2a46c5a5fd1b291
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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