Lithium Hydroxide → US9249085, I(ab)

HRID 1771740Notes

Reaction equation

HRID 1771740 reaction equation
[F:1][C:2]1[C:15]([NH:16][CH2:17][C:18]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=3)[CH:21]=[CH:20][C:19]=2[F:31])=[C:14]([F:32])[C:13]([CH3:33])=[CH:12][C:3]=1[O:4][CH2:5][C:6]([O:8]C(C)C)=[O:7].[Li+].[OH-]>C1COCC1>[F:1][C:2]1[C:15]([NH:16][CH2:17][C:18]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=3)[CH:21]=[CH:20][C:19]=2[F:31])=[C:14]([F:32])[C:13]([CH3:33])=[CH:12][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 89443608HCID 89443608, compound

Product 1

HCID 89443989US9249085, I(ab)Yield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl 2-[2,4-difluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-5-methyl-phenoxy]acetate (194 mg, 0.42 mmol, 1.0 eq) in THF (10 mL) was added LiOH (2M aqueous solution, 5 mL, 5 mmol). The reaction mixture was stirred at room temperature overnight. The THF was removed under reduced pressure and the pH of the aqueous phase adjusted to pH 5 by addition of diluted HCl. The solid that formed was collected by filtration, washed with water and dried in vacuo to give the title compound as a white solid (61 mg, 91%).

Workup

  1. customThe THF was removed under reduced pressure
  2. additionthe pH of the aqueous phase adjusted to pH 5 by addition of diluted HCl
  3. customThe solid that formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-fb3e1701d9aa4cb59d836ec92b1a8e44
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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