Lithium Hydroxide → HCID 89443843, compound

HRID 1771821Notes

Reaction equation

HRID 1771821 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([CH3:34])[C:12]([CH3:33])=[C:13]([CH2:15][NH:16][C:17]3[C:18]([F:32])=[C:19]([CH:28]=[CH:29][C:30]=3[F:31])[O:20][CH2:21][C:22]([O:24]C(C)C)=[O:23])[CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8].[Li+].[OH-]>C1COCC1.CO>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([CH3:34])[C:12]([CH3:33])=[C:13]([CH2:15][NH:16][C:17]3[C:18]([F:32])=[C:19]([CH:28]=[CH:29][C:30]=3[F:31])[O:20][CH2:21][C:22]([OH:24])=[O:23])[CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 89444080Isopropyl 2-[3-[[5-(3,4-difluorophenyl)-2,3-dimethyl-phenyl]methylamino]-2,4-difluoro-phenoxy]acetate

Product 1

HCID 89443843HCID 89443843, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl 2-[3-[[5-(3,4-difluorophenyl)-2,3-dimethyl-phenyl]methylamino]-2,4-difluoro-phenoxy]acetate (70 mg, 0.15 mmol, 1.0 eq) in a mixture of THF (1.5 mL) and MeOH (0.5 mL) was added LiOH (2M aqueous solution, 1.5 mL, 3.0 mmol). The reaction was stirred at room temperature for 1 h then the organic solvent was removed under reduced pressure. The remaining aqueous solution was diluted with water and the solution acidified to pH 4-5 with 3M HCl. The mixture was extracted with EtOAc and the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a white solid (63 mg, 99%).

Workup

  1. customthe organic solvent was removed under reduced pressure
  2. additionThe remaining aqueous solution was diluted with water
  3. extractionThe mixture was extracted with EtOAc
  4. washthe combined organic extracts were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-e314822a7c0945c1a07617f157f596bf
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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