Lithium Hydroxide → US9249085, I(af)

HRID 1771760Notes

Reaction equation

HRID 1771760 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][C:8]([O:10]C(C)C)=[O:9])=[C:4]([CH3:16])[C:3]=1[NH:17][CH2:18][C:19]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[CH:22]=[C:21]([CH3:32])[C:20]=1[O:33][CH3:34].[Li+].[OH-]>C1COCC1>[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[C:4]([CH3:16])[C:3]=1[NH:17][CH2:18][C:19]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[CH:22]=[C:21]([CH3:32])[C:20]=1[O:33][CH3:34]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 89445418Isopropyl 2-[4-fluoro-3-[[5-(3-fluorophenyl)-2-methoxy-3-methyl-phenyl]methylamino]-2-methyl-phenoxy]acetate

Product 1

HCID 89443809US9249085, I(af)Yield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl 2-[4-fluoro-3-[[5-(3-fluorophenyl)-2-methoxy-3-methyl-phenyl]methylamino]-2-methyl-phenoxy]acetate (64 mg, 0.2 mmol, 1.0 eq) in THF (2 mL) was added LiOH (2M aqueous solution, 2.0 mL, 4.0 mmol). The reaction mixture was stirred at room temperature for 1 h. The THF was removed and the pH of the aqueous solution that remained adjusted to pH 4-5 with diluted HCl. The aqueous layer was extracted with EtOAc, the organic extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a white solid (30 mg, 50%).

Workup

  1. customThe THF was removed
  2. extractionThe aqueous layer was extracted with EtOAc
  3. extractionthe organic extract
  4. washwas washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-d88db079fd624249be2e8e9494b257f0
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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