Sodium Hydroxide → US9249085, I(ao)

HRID 1771815Notes

Reaction equation

HRID 1771815 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:15][NH:16][C:17]3[C:18]([CH3:32])=[C:19]([CH:28]=[CH:29][C:30]=3[CH3:31])[O:20][CH2:21][C:22]([O:24]C(C)C)=[O:23])[CH:11]=[C:12]([OH:14])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:15][NH:16][C:17]3[C:18]([CH3:32])=[C:19]([CH:28]=[CH:29][C:30]=3[CH3:31])[O:20][CH2:21][C:22]([OH:24])=[O:23])[CH:11]=[C:12]([OH:14])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89443953Isopropyl 2-[3-[[3-(3-fluorophenyl)-5-hydroxy-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate

Product 1

HCID 89443827US9249085, I(ao)Yield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl 2-[3-[[3-(3-fluorophenyl)-5-hydroxy-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate (100 mg, 0.22 mmol, 1.0 eq) in THF (10 mL) at 0° C. was added NaOH (1M aqueous solution, 3 mL, 3 mmol). The reaction mixture was stirred at room temperature overnight then the THF was removed under reduced pressure. The remaining aqueous solution was poured into water and adjusted to pH 4-6 by addition of diluted HCl. The solid that precipitated was collected by filtration, washed with water and dried in vacuo to give the title compound as a yellow solid (60 mg, 66%).

Workup

  1. customthe THF was removed under reduced pressure
  2. additionThe remaining aqueous solution was poured into water
  3. additionadjusted to pH 4-6 by addition of diluted HCl
  4. customThe solid that precipitated
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-20ff4203124e4ee2b10c0433d1202571
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

Loading…