Sodium Hydroxide → US9249085, I(ad)

HRID 1771750Notes

Reaction equation

HRID 1771750 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[F:33].[OH-].[Na+]>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[F:33]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89443404Isopropyl 2-[4-fluoro-3-[[2-fluoro-5-(3-fluorophenyl)-3-methyl-phenyl]methylamino]-2-methyl-phenoxy]acetate

Product 1

HCID 89443583US9249085, I(ad)Yield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl 2-[4-fluoro-3-[[2-fluoro-5-(3-fluorophenyl)-3-methyl-phenyl]methylamino]-2-methyl-phenoxy]acetate (150 mg, 0.33 mmol) in THF (6 mL) was added NaOH (1M aqueous solution, 4.0 mL, 4.0 mmol). The reaction mixture was stirred at room temperature for 2 h, then the THF removed under reduced pressure. The remaining aqueous solution was adjusted to pH 3-4 with diluted HCl and the solid that precipitated collected by filtration, washed with water and dried in vacuo to give the title compound as a white solid (100 mg, 74%).

Workup

  1. customthe THF removed under reduced pressure
  2. customthe solid that precipitated
  3. filtrationcollected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-021e3a78a7db4c638a411b4053bc73c5
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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