Sodium Hydroxide → US9249085, I(ap)

HRID 1771816Notes

Reaction equation

HRID 1771816 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:16][NH:17][C:18]3[C:19]([CH3:33])=[C:20]([CH:29]=[CH:30][C:31]=3[CH3:32])[O:21][CH2:22][C:23]([O:25]C(C)C)=[O:24])[CH:11]=[C:12]([O:14][CH3:15])[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]([CH2:16][NH:17][C:18]3[C:19]([CH3:33])=[C:20]([CH:29]=[CH:30][C:31]=3[CH3:32])[O:21][CH2:22][C:23]([OH:25])=[O:24])[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89443955Isopropyl 2-[3-[[3-(3-fluorophenyl)-5-methoxy-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate

Product 1

HCID 89443767US9249085, I(ap)Yield 66.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl 2-[3-[[3-(3-fluorophenyl)-5-methoxy-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate (II(at)) (100 mg, 0.22 mmol, 1.0 eq) in THF (10 mL) was added NaOH (1M aqueous solution, 3.0 mL, 3.0 mmol). The reaction mixture was stirred at room temperature for 2 h, then the THF was removed under reduced pressure. The remaining aqueous solution was adjusted to pH 3-4 by the 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 adjusted to pH 3-4 by the addition of diluted HCl
  3. customThe solid that precipitated
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-35dfc59c85e44f1eb395a970fce85037
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

Loading…