Water → US9249085, I(au)

HRID 1771837Notes

Reaction equation

HRID 1771837 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[C:18]([F:32])=[C:19]([CH:28]=[CH:29][C:30]=1[F:31])[O:20][CH2:21][C:22]([O:24]C(C)C)=[O:23].[Li+].[OH-].O>C1COCC1>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[C:18]([F:32])=[C:19]([CH:28]=[CH:29][C:30]=1[F:31])[O:20][CH2:21][C:22]([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 89444175Isopropyl 2-[3-[(2,3-dimethyl-5-phenyl-phenyl)methylamino]-2,4-difluoro-phenoxy]acetate

Product 1

HCID 89444124US9249085, I(au)Yield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl 2-[3-[(2,3-dimethyl-5-phenyl-phenyl)methylamino]-2,4-difluoro-phenoxy]acetate (110 mg, 0.25 mmol, 1.0 eq) in THF (4 mL) was added LiOH (52 mg, 1.2 mmol, 5 eq) and water (3 mL) and the reaction mixture stirred at room temperature for 1 h. The THF was removed under reduced pressure and the remaining aqueous solution was adjusted to pH 4-5 by addition of 1M HCl. The mixture was extracted with EtOAc and the combined organic extracts washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a yellow oil (80 mg, 80%).

Workup

  1. customThe THF was removed under reduced pressure
  2. additionthe remaining aqueous solution was adjusted to pH 4-5 by addition of 1M HCl
  3. extractionThe mixture was extracted with EtOAc
  4. washthe combined organic extracts washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-5ede37b9ed2346f1b95693ed9e45e801
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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