Lithium Hydroxide → US9249085, I(ae)

HRID 1771756Notes

Reaction equation

HRID 1771756 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][C:8]([O:10]C(C)C)=[O:9])=[C:4]([CH3:16])[C:3]=1[NH:17][CH2:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)[CH:20]=1.[Li+].[OH-]>C1COCC1>[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[C:4]([CH3:16])[C:3]=1[NH:17][CH2:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)[CH:20]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 89443834Isopropyl 2-[4-fluoro-3-[[3-(3-fluorophenyl)-5-methyl-phenyl]methylamino]-2-methyl-phenoxy]acetate

Product 1

HCID 89443716US9249085, I(ae)Yield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl 2-[4-fluoro-3-[[3-(3-fluorophenyl)-5-methyl-phenyl]methylamino]-2-methyl-phenoxy]acetate (200 mg, 0.46 mmol, 1.0 eq) in THF (10 mL) was added LiOH (2M aqueous solution, 4 mL, 8.0 mmol). The reaction mixture was stirred at room temperature for 2 h then the THF was removed in vacuo. The pH of the aqueous solution that remained was adjusted to pH 5 by addition of 3M HCl. The solid precipitate that formed was collected by filtration, washed with water and dried in vacuo to give the title compound as a yellow solid (150 mg, 83%).

Workup

  1. customthe THF was removed in vacuo
  2. additionThe pH of the aqueous solution that remained was adjusted to pH 5 by addition of 3M HCl
  3. customThe solid precipitate that formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-2bf46659bf4e4de9b73d30d3379f3ae9
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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