Sodium Hydroxide → US9249085, I(aa)

HRID 1771733Notes

Reaction equation

HRID 1771733 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]=[C:20]([F:31])[C:19]=2[CH3:32])=[C:14]([F:33])[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][C:6]([O:8]C(C)C)=[O:7].[OH-].[Na+]>C1COCC1.CO>[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]=[C:20]([F:31])[C:19]=2[CH3:32])=[C:14]([F:33])[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 89443922HCID 89443922, compound

Product 1

HCID 89443671US9249085, I(aa)Yield 38.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl 2-[2,4-difluoro-3-[[3-fluoro-5-(3-fluorophenyl)-2-methyl-phenyl]methylamino]phenoxy]acetate (300 mg, 0.65 mmol, 1.0 eq) in a mixture of THF (10 mL) and MeOH (10 mL) was added NaOH (2M aqueous solution, 10 mL). The reaction mixture was stirred at room temperature for 3 h. The THF was evaporated in vacuo and the pH of the aqueous phase adjusted pH 3 with diluted HCl. The solid precipitate that formed was collected by filtration, washed with water and dried to give the title compound as a white solid (104 mg, 38%).

Workup

  1. customThe THF was evaporated in vacuo
  2. customThe solid precipitate that formed
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-d0c9444f3be1457aa469a75c5c9e9b46
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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