Sodium Hydroxide → 2-[2,4-Difluoro-3-[[3-(3-fluorophenyl)-5-methyl-phenyl]methylamino]phenoxy]acetic acid

HRID 1771604Notes

Reaction equation

HRID 1771604 reaction equation
[F:1][C:2]1[C:15]([NH:16][CH2:17][C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[CH:19]=2)=[C:14]([F:32])[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][C:6]([O:8]C(C)C)=[O:7].[OH-].[Na+]>C1COCC1>[F:1][C:2]1[C:15]([NH:16][CH2:17][C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[CH:19]=2)=[C:14]([F:32])[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89443771Isopropyl 2-[2,4-difluoro-3-[[3-(3-fluorophenyl)-5-methyl-phenyl]methylamino]phenoxy]acetate

Product 1

HCID 715155182-[2,4-Difluoro-3-[[3-(3-fluorophenyl)-5-methyl-phenyl]methylamino]phenoxy]acetic acidYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of isopropyl 2-[2,4-difluoro-3-[[3-(3-fluorophenyl)-5-methylphenyl]methylamino]phenoxy]acetate (127 mg, 0.29 mmol, 1.0 eq) in THF (3 mL) was added NaOH (2M aqueous solution, 0.57 mL, 1.15 mmol, 4.0 eq) at room temperature. The reaction was stirred at room temperature for 1 h and then the THF removed in vacuo and the aqueous residue adjusted to pH 4 by addition of 1M HCl. The precipitate was collected by filtration, dried in vacuo and crystallized from CH2Cl2 and petroleum ether to give the title compound (I(d)) as a white solid (50 mg, 44%).

Workup

  1. customthe THF removed in vacuo
  2. additionthe aqueous residue adjusted to pH 4 by addition of 1M HCl
  3. filtrationThe precipitate was collected by filtration
  4. customdried in vacuo
  5. customcrystallized from CH2Cl2 and petroleum ether

Sources & evidence

ORD record
ord-8168e51b4bc14896aec9a47d5b473305
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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