Sodium Hydroxide → HCID 89443417, compound

HRID 1771649Notes

Reaction equation

HRID 1771649 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[C:18]([F:31])=[C:19]([CH:27]=[CH:28][C:29]=1[F:30])[O:20][CH2:21][C:22]([O:24]CC)=[O:23].[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[C:18]([F:31])=[C:19]([CH:27]=[CH:28][C:29]=1[F:30])[O:20][CH2:21][C:22]([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89443391Ethyl 2-[3-[[2-chloro-5-(3-fluorophenyl)phenyl]methylamino]-2,4-difluoro-phenoxy]acetate

Product 1

HCID 89443417HCID 89443417, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[3-[[2-chloro-5-(3-fluorophenyl)phenyl]methylamino]-2,4-difluoro-phenoxy]acetate (120 mg, 0.27 mmol, 1.0 eq) in THF (8 mL) was added NaOH (1M aqueous solution, 3 mL, 3 mmol, 11.0 eq). The reaction was stirred at room temperature for 2 h. The THF was removed in vacuo and the residue acidified to pH 5 by addition of 1M HCl. The precipitate that formed was collected by filtration, washed with water and dried to give the title compound (I(l)) (100 mg, 88%).

Workup

  1. customThe THF was removed in vacuo
  2. additionthe residue acidified to pH 5 by addition of 1M HCl
  3. customThe precipitate that formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-032af362772a47baaf599d3154798304
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

Loading…