Sodium Hydroxide → 2-((S)-6-((R)-4-(2,6-Dimethyl-4-(3-(methylsulfonyl)propyl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

HRID 237720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 237720
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:7]=[C:6]([CH3:17])[C:5]=1[C:18]1[CH:26]=[CH:25][C:24]([F:27])=[C:23]2[C:19]=1[CH2:20][CH2:21][C@H:22]2[O:28][C:29]1[CH:42]=[CH:41][C:32]2[C@H:33]([CH2:36][C:37]([O:39]C)=[O:38])[CH2:34][O:35][C:31]=2[CH:30]=1>CO>[CH3:17][C:6]1[CH:7]=[C:8]([CH2:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:9]=[C:4]([CH3:3])[C:5]=1[C:18]1[CH:26]=[CH:25][C:24]([F:27])=[C:23]2[C:19]=1[CH2:20][CH2:21][C@H:22]2[O:28][C:29]1[CH:42]=[CH:41][C:32]2[C@H:33]([CH2:36][C:37]([OH:39])=[O:38])[CH2:34][O:35][C:31]=2[CH:30]=1

Komponenten

4

Edukt 2

HCID 14798Sodium Hydroxide2×HCID 86697206Methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(3-(methylsulfonyl)propyl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Produkt 1

HCID 866973892-((S)-6-((R)-4-(2,6-Dimethyl-4-(3-(methylsulfonyl)propyl)phenyl)-7-fluoro-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 (50 μL) is added to a solution of methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(3-(methylsulfonyl)propyl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (20 mg) in methanol (2 mL). The mixture is stirred at room temperature for 12 hours and at 50° C. for 2 days. 1 M aqueous NaOH solution (18 μL) is added and the mixture is stirred at 50° C. for 2 hours. 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 organic phase is dried (MgSO4). The solvent is evaporated and the residue is purified by HPLC on reversed phase to give the title compound. Yield: 7 mg; LC (method 8): tR=0.34 min; Mass spectrum (ESI+): m/z=553 [M+H]+.

Aufarbeitung

  1. stirringthe mixture is stirred at 50° C. for 2 hours
  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. dry with materialthe organic phase is dried (MgSO4)
  6. customThe solvent is evaporated
  7. customthe residue is purified by HPLC on reversed phase

Quellen und Nachweise

ORD-Eintrag
ord-0b29ddbfde6f48e48297727ec81f5ea6
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642585B2

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