Sodium Hydroxide → 2-[4-Fluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2-methyl-phenoxy]acetic acid
Reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10]CC)=[O:9])=[C:4]([CH3:15])[C:3]=1[NH:16][CH2:17][C:18]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[CH:21]=[CH:20][C:19]=1[F:31].[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[C:4]([CH3:15])[C:3]=1[NH:16][CH2:17][C:18]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[CH:21]=[CH:20][C:19]=1[F:31]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ethyl 2-[4-fluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2-methyl-phenoxy]acetate (200 mg, 0.466 mmol, 1.0 eq) in THF (8 mL) was added NaOH (1M aqueous solution, 4 mL, 4.0 mmol, 9.0 eq) at 0° C. The reaction mixture was stirred at room temperature for 1 h, then the organic solvent removed under reduced pressure and the aqueous solution diluted with water and adjusted to pH 4-6 by addition of diluted HCl. The precipitate that formed was collected by filtration, washed with water and dried in vacuo to give the title compound (I(m)) as a solid (150 mg, 80%).
Workup
- customthe organic solvent removed under reduced pressure
- additionthe aqueous solution diluted with water
- additionadjusted to pH 4-6 by addition of diluted HCl
- customThe precipitate that formed
- filtrationwas collected by filtration
- washwashed with water
- customdried in vacuo
Sources & evidence
- ORD record
- ord-d1c152c712e5449d9d1d24f1b40250ac
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249085B2
Reaction notes
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