Sodium Hydroxide → HCID 89444254, compound

HRID 1771691Notes

Reaction equation

HRID 1771691 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:6][CH:5]=[C:4]([F:15])[C:3]=1[CH2:16][NH:17][C:18]1[C:19]([F:32])=[C:20]([CH:28]=[CH:29][C:30]=1[F:31])[O:21][CH2:22][C:23]([O:25]CC)=[O:24].[OH-].[Na+]>C1COCC1>[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:6][CH:5]=[C:4]([F:15])[C:3]=1[CH2:16][NH:17][C:18]1[C:19]([F:32])=[C:20]([CH:28]=[CH:29][C:30]=1[F:31])[O:21][CH2:22][C:23]([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89444218HCID 89444218, compound

Product 1

HCID 89444254HCID 89444254, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[3-[[2,6-difluoro-3-(3-fluorophenyl)phenyl]methylamino]-2,4-difluoro-phenoxy]acetate (240 mg, 0.53 mmol, 1.0 eq) in THF (10 mL) was added a solution of aqueous NaOH (1M aqueous solution, 5 mL, 5 mmol, 9.4 eq). The reaction mixture was stirred at room temperature for 3 h. The organic solvent was removed in vacuo and the residue diluted with water and adjusted to pH 5-6 by addition of diluted HCl. The precipitate that formed was collected by filtration, washed with water and dried in vacuo to give the title compound as a solid (180 mg, 80%).

Workup

  1. customThe organic solvent was removed in vacuo
  2. additionthe residue diluted with water
  3. additionadjusted to pH 5-6 by addition of diluted HCl
  4. customThe precipitate that formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-e4f08464cc8d4d60863f53e7a04c6358
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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