Lithium Hydroxide → HCID 58042449, compound

HRID 2048061Notes

Reaction equation

HRID 2048061 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:13][C:14]2[C:24]([F:25])=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[C:16]([F:26])[CH:15]=2)[CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH:10]([CH3:12])[CH3:11].[OH-].[Li+].C1COCC1>O>[Cl:1][C:2]1[CH:3]=[C:4]([O:13][C:14]2[C:24]([F:25])=[CH:23][C:17]([C:18]([OH:20])=[O:19])=[C:16]([F:26])[CH:15]=2)[CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH:10]([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58042433HCID 58042433, compound

Product 1

HCID 58042449HCID 58042449, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 4-[(5-chloro-6-isobutoxypyridin-3-yl)oxy]-2,5-difluorobenzoate (Preparation 38, 150 mg, 0.389 mmol) and lithium hydroxide (250 mg, 10.44 mmol) were dissolved in water (2.5 mL) and THF (2.5 mL) and stirred at room temperature for 72 hours. The reaction mixture was concentrated in vacuo. The residue was dissolved in EtOAc (10 mL), washed with water (10 mL) and aqueous HCl (2 M, 10 mL), then was dried over sodium sulfate, filtered and concentrated in vacuo to yield the title compound as a white solid (140 mg, 100%):

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (10 mL)
  3. washwashed with water (10 mL) and aqueous HCl (2 M, 10 mL)
  4. dry with materialwas dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ba5c84201ba246c5bc7e32f0f6256586
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

Loading…