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

HRID 1771677Notes

Reaction equation

HRID 1771677 reaction equation
[F:1][C:2]1[C:14]([NH:15][CH2:16][C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[CH:18]=2)=[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]([O:23][CH3:24])[CH:20]=[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[CH:18]=2)=[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 89443604Ethyl 2-[2,4-difluoro-3-[[3-(3-fluorophenyl)-5-methoxy-phenyl]methylamino]phenoxy]acetate

Product 1

HCID 894441322-[2,4-Difluoro-3-[[3-(3-fluorophenyl)-5-methoxy-phenyl]methylamino]phenoxy]acetic acidYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[2,4-difluoro-3-[[3-(3-fluorophenyl)-5-methoxy-phenyl]methylamino]phenoxy]acetate (see example 16) (200 mg, 0.45 mmol, 1.0 eq) in THF (10 mL) was added an aqueous solution of NaOH (1 M aqueous solution, 4 mL, 4 mmol, 8.9 eq) at 0° C. The reaction mixture was stirred at room temperature for 3 h. The organic solvent was removed water added and the pH adjusted to pH 4-6 by addition of 1M HCl. The solid that precipitated was collected by filtration and dried in vacuo to give the title compound as a solid (150 mg, 80%).

Workup

  1. customThe organic solvent was removed water
  2. additionadded
  3. additionthe pH adjusted to pH 4-6 by addition of 1M HCl
  4. customThe solid that precipitated
  5. filtrationwas collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-b0d5c29df3934604976353da6ccdb74b
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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