Lithium Hydroxide → US9249085, I(am)

HRID 1771803Notes

Reaction equation

HRID 1771803 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:6][C:5]([CH3:15])=[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]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:6][C:5]([CH3:15])=[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 89443725Isopropyl 2-[3-[[2-fluoro-3-(3-fluorophenyl)-5-methyl-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate

Product 1

HCID 89443873US9249085, I(am)Yield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl 2-[3-[[2-fluoro-3-(3-fluorophenyl)-5-methyl-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate (80 mg, 0.18 mmol, 1.0 eq) in THF (8 mL) at 0° C. was added LiOH (2M aqueous solution, 4 mL, 8.0 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. The THF was removed and the remaining aqueous solution was diluted with water. The pH was adjusted to pH 4-6 by addition of diluted HCl. The solid precipitate that formed was collected by filtration, washed with water and dried in vacuo to give target compound as a yellow solid (30 mg, 41%).

Workup

  1. customThe THF was removed
  2. additionthe remaining aqueous solution was diluted with water
  3. additionThe pH was adjusted to pH 4-6 by addition of diluted 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-714660e684c04824925cf676593423d7
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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