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

HRID 237717

Reaktionsgleichung

Reaktionsgleichung von HRID 237717
[OH-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:28]2[C:33]([CH3:34])=[CH:32][C:31]([CH2:35][CH2:36][C:37]([OH:40])([CH3:39])[CH3:38])=[CH:30][C:29]=2[CH3:41])=[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]([CH2:35][CH2:36][C:37]([OH:40])([CH3:38])[CH3:39])=[CH:30][C:29]=2[CH3:41])=[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

Komponenten

4

Edukt 2

HCID 14798Sodium Hydroxide2×HCID 86697201Methyl 2-((S)-6-((R)-7-fluoro-4-(4-(3-hydroxy-3-methylbutyl)-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Produkt 1

HCID 866973872-((S)-6-((R)-7-Fluoro-4-(4-(3-hydroxy-3-methylbutyl)-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

1 M aqueous NaOH solution (310 μL) is added to a solution of methyl 2-((S)-6-((R)-7-fluoro-4-(4-(3-hydroxy-3-methylbutyl)-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (110 mg) in methanol (4 mL). The mixture is stirred at room temperature for 12 hours and at 50° C. for 2 days. 1 M aqueous NaOH solution (100 μL) is added and the mixture is stirred at 50° C. for 1 hour. Methanol is evaporated in vacuo, the residue is diluted with water and neutralized with 1 M aqueous HCl. The resulting mixture is extracted with ethyl acetate, and the combined organic phases are washed with brine and dried (MgSO4). The solvent is evaporated to give the title compound. Yield: 80 mg; LC (method 8): tR=0.59 min; Mass spectrum (ESI+): m/z=519 [M+H]+.

Aufarbeitung

  1. stirringthe mixture is stirred at 50° C. for 1 hour
  2. customMethanol is evaporated in vacuo
  3. additionthe residue is diluted with water and neutralized with 1 M aqueous HCl
  4. extractionThe resulting mixture is extracted with ethyl acetate
  5. washthe combined organic phases are washed with brine
  6. dry with materialdried (MgSO4)
  7. customThe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-efbe6109626048c3a398ab640781c4f8
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642585B2

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