Lithium Hydroxide → US9249085, I(ar)

HRID 1771826Notes

Reaction equation

HRID 1771826 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([CH3:34])[C:12]([CH3:33])=[C:13]([CH2:15][NH:16][C:17]3[C:18]([F:32])=[C:19]([CH:28]=[CH:29][C:30]=3[F:31])[O:20][CH2:21][C:22]([O:24]C(C)C)=[O:23])[CH:14]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[Li+].[OH-]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([CH3:34])[C:12]([CH3:33])=[C:13]([CH2:15][NH:16][C:17]3[C:18]([F:32])=[C:19]([CH:28]=[CH:29][C:30]=3[F:31])[O:20][CH2:21][C:22]([OH:24])=[O:23])[CH:14]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 89445489Isopropyl 2-[3-[[5-(3,5-difluorophenyl)-2,3-dimethyl-phenyl]methylamino]-2,4-difluoro-phenoxy]acetate

Product 1

HCID 89443711US9249085, I(ar)Yield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl 2-[3-[[5-(3,5-difluorophenyl)-2,3-dimethyl-phenyl]methylamino]-2,4-difluoro-phenoxy]acetate (23 mg, 0.048 mmol, 1.0 eq) in THF (3 mL) at 0° C. was added LiOH (2M aqueous solution, 1 mL, 2.0 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. The THF was removed under reduced pressure and the remaining aqueous solution was adjusted to pH 3 by addition of 3M HCl. The resulting mixture was extracted with EtOAc and the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a yellow solid (20 mg, 95%).

Workup

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

Sources & evidence

ORD record
ord-adf2c93b817643e2a1e2658626c64f47
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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