Sodium Hydroxide → 2-((S)-6-((R)-7-Fluoro-4-(4-(3-hydroxy-3-methylbutoxy)-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

HRID 237698Notes

Reaction equation

HRID 237698 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:28]2[C:33]([CH3:34])=[CH:32][C:31]([O:35][CH2:36][CH2:37][C:38]([OH:41])([CH3:40])[CH3:39])=[CH:30][C:29]=2[CH3:42])=[C:8]2[C:12]=1[C@H:11]([O:13][C:14]1[CH:27]=[CH:26][C:17]3[C@H:18]([CH2:21][C:22]([O:24]C)=[O:23])[CH2:19][O:20][C:16]=3[CH:15]=1)[CH2:10][CH2:9]2>CO>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:28]2[C:33]([CH3:34])=[CH:32][C:31]([O:35][CH2:36][CH2:37][C:38]([OH:41])([CH3:39])[CH3:40])=[CH:30][C:29]=2[CH3:42])=[C:8]2[C:12]=1[C@H:11]([O:13][C:14]1[CH:27]=[CH:26][C:17]3[C@H:18]([CH2:21][C:22]([OH:24])=[O:23])[CH2:19][O:20][C:16]=3[CH:15]=1)[CH2:10][CH2:9]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86697111Methyl 2-((S)-6-((R)-7-fluoro-4-(4-(3-hydroxy-3-methylbutoxy)-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 717389952-((S)-6-((R)-7-Fluoro-4-(4-(3-hydroxy-3-methylbutoxy)-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 M aqueous NaOH solution (420 μL) is added to a solution of methyl 2-((S)-6-((R)-7-fluoro-4-(4-(3-hydroxy-3-methylbutoxy)-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (155 mg) in methanol (4 mL) at room temperature. The mixture is stirred at room temperature for 12 hours. The organic solvents are evaporated in vacuo. The residue is diluted with water and neutralized with 1 M aqueous HCl solution (420 μL). The mixture is stirred for 1 hour. The precipitate formed is filtered off, washed with water and dried in vacuo to give the title compound. Yield: 110 mg; LC (method 4): tR=1.85 min; Mass spectrum (ESI+): m/z=535 [M+H]+.

Workup

  1. customThe organic solvents are evaporated in vacuo
  2. additionThe residue is diluted with water and neutralized with 1 M aqueous HCl solution (420 μL)
  3. stirringThe mixture is stirred for 1 hour
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-fdd9576e9b8a47faa2e6d091e9fc5274
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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