Lithium Hydroxide → US9249085, I(ag)

HRID 1771764Notes

Reaction equation

HRID 1771764 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)=[CH:4][C:3]=1[CH2:16][NH:17][C:18]1[C:19]([CH3:33])=[C:20]([CH:29]=[CH:30][C:31]=1[CH3:32])[O:21][CH2:22][C:23]([O:25]C(C)C)=[O:24].[Li+].[OH-]>C1COCC1>[F:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)=[CH:4][C:3]=1[CH2:16][NH:17][C:18]1[C:19]([CH3:33])=[C:20]([CH:29]=[CH:30][C:31]=1[CH3:32])[O:21][CH2:22][C:23]([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 89443796Isopropyl 2-[3-[[2-fluoro-5-(3-fluorophenyl)-3-methyl-phenyl]methyl amino]-2,4-dimethyl-phenoxy]acetate

Product 1

HCID 89443554US9249085, I(ag)Yield 64.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl 2-[3-[[2-fluoro-5-(3-fluorophenyl)-3-methyl-phenyl]methyl amino]-2,4-dimethyl-phenoxy]acetate (70 mg, 0.15 mmol, 1.0 eq) in THF (5 mL) at 0° C. was added LiOH (2M aqueous solution, 2.0 mL, 4.0 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The THF was removed in vacuo and the remaining aqueous mixture diluted with water and adjusted to pH 5 by addition of 3M HCl. The solid that precipitated was collected by filtration and dried in vacuo to give the title compound as a yellow solid (40 mg, 63%).

Workup

  1. customThe THF was removed in vacuo
  2. additionthe remaining aqueous mixture diluted with water
  3. additionadjusted to pH 5 by addition of 3M HCl
  4. customThe solid that precipitated
  5. filtrationwas collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-bdfc99ab6ffb44a4876ebcf35fd6c77b
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

Loading…