Sodium Hydroxide → US9249085, I(ak)

HRID 1771795Notes

Reaction equation

HRID 1771795 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH3:33])[C:11]([CH3:32])=[C:12]([CH2:14][NH:15][C:16]3[C:17]([CH3:31])=[C:18]([CH:27]=[CH:28][C:29]=3[CH3:30])[O:19][CH2:20][C:21]([O:23]C(C)C)=[O:22])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>C1COCC1.CO>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH3:33])[C:11]([CH3:32])=[C:12]([CH2:14][NH:15][C:16]3[C:17]([CH3:31])=[C:18]([CH:27]=[CH:28][C:29]=3[CH3:30])[O:19][CH2:20][C:21]([OH:23])=[O:22])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 89443588Isopropyl 2-[3-[[5-(3-fluorophenyl)-2,3-dimethyl-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate

Product 1

HCID 89443841US9249085, I(ak)Yield 28.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl 2-[3-[[5-(3-fluorophenyl)-2,3-dimethyl-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate (80 mg, 0.17 mmol, 1.0 eq) in a mixture of THF (5 mL) and MeOH (5 mL) was added NaOH (2M aqueous solution, 3 mL, 6.0 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The organic solvent was removed in vacuo and the remaining aqueous solution diluted with water and acidified to pH 4-6 with diluted HCl. The solid precipitate that formed was collected by filtration, washed with water and dried in vacuo to give the title compound as a white solid (20 mg, 27%).

Workup

  1. customThe organic solvent was removed in vacuo
  2. additionthe remaining aqueous solution diluted with water
  3. customThe solid precipitate that formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-94b47ff8a8504a9a88e43b9f6a1b3b12
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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