Lithium Hydroxide → US9249085, I(aj)

HRID 1771791Notes

Reaction equation

HRID 1771791 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]([CH3:14])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[Li+].[OH-]>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]([CH3:14])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 89443749Isopropyl 2-[3-[[3-(3-fluorophenyl)-5-methyl-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate

Product 1

HCID 89443614US9249085, I(aj)Yield 68.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl 2-[3-[[3-(3-fluorophenyl)-5-methyl-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate (114 mg, 0.26 mmol, 1.0 eq) in THF (10 mL) at 0° C. was added LiOH (2M aqueous solution, 4 mL, 8 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. The THF was removed under reduced pressure and the aqueous solution that remained was diluted with water and adjusted to pH 4-6 by the addition of dilute HCl. The solid precipitate that formed was collected by filtration, washed with water and dried in vacuo to give title compound as a yellow solid (70 mg, 68%).

Workup

  1. customThe THF was removed under reduced pressure
  2. additionthe aqueous solution that remained was diluted with water
  3. additionadjusted to pH 4-6 by the addition of dilute HCl
  4. customThe solid precipitate that formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-b63be1a99d774864b21198ed841b26d1
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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