Lithium Hydroxide → US9249085, I(al)

HRID 1771799Notes

Reaction equation

HRID 1771799 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH3:34])[C:11]([O:32][CH3:33])=[C:12]([CH2:14][NH:15][C:16]3[C:17]([CH3:31])=[C:18]([CH:27]=[CH:28][C:29]=3[CH3:30])[O:19][CH2:20][C:21]([O:23]C(C)C)=[O:22])[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]([CH3:34])[C:11]([O:32][CH3:33])=[C:12]([CH2:14][NH:15][C:16]3[C:17]([CH3:31])=[C:18]([CH:27]=[CH:28][C:29]=3[CH3:30])[O:19][CH2:20][C:21]([OH:23])=[O:22])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 89443576Isopropyl 2-[3-[[5-(3-fluorophenyl)-2-methoxy-3-methyl-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate

Product 1

HCID 89443871US9249085, I(al)Yield 21.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl 2-[3-[[5-(3-fluorophenyl)-2-methoxy-3-methyl-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate (155 mg, 0.33 mmol, 1.0 eq) in THF (4 mL) was added LiOH (2M aqueous solution, 4 mL, 8 mmol). The reaction mixture was stirred at room temperature for 2 h then the THF was removed under reduced pressure. The aqueous solution that remained was diluted with water and the pH adjusted to 4-6 with diluted HCl. The solid precipitate that formed was collected by filtration, washed with water and dried in vacuo to give a partially purified product. This material was further purified by preparative HPLC to give the title compound as a yellow solid (30 mg, 21%).

Workup

  1. customthe THF was removed under reduced pressure
  2. additionThe aqueous solution that remained was diluted with water
  3. customThe solid precipitate that formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried in vacuo
  7. customto give a partially purified product
  8. customThis material was further purified by preparative HPLC

Sources & evidence

ORD record
ord-519031b3cdcc40c39657f81386abd1d7
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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