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

HRID 237695
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 237695
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2([CH3:16])[CH2:15][O:14][CH2:13]2)[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.O.Cl.C(#N)C.O>[CH3:3][C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2([CH3:16])[CH2:13][O:14][CH2:15]2)[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]([OH:39])=[O:38])[CH2:34][O:35][C:31]=2[CH:30]=1
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Komponenten

7

Edukt 2

HCID 14798Sodium HydroxideHCID 86697105Methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-((3-methyloxetan-3-yl)methoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Produkt 1

HCID 717389332-((S)-6-((R)-4-(2,6-dimethyl-4-((3-methyloxetan-3-yl)methoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 313
Hydrochloric Acid
Lösungsmittel
HCID 887MethanolLösungsmittel
HCID 962WaterLösungsmittel
HCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

1 M aqueous NaOH solution (1.15 mL) is added to a solution of methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-((3-methyloxetan-3-yl)methoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (420 mg) in methanol (12 mL) at room temperature. The mixture is stirred at room temperature for 48 hours. The mixture is diluted with water and neutralized with 1 M aqueous HCl solution (1.15 mL). The resulting mixture is extracted with ethyl acetate, and the combined extract is washed with brine and dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30→20:80). The product thus obtained is dissolved in acetonitrile/water (1:1) and lyophilized to give the title compound. Yield: 265 mg; LC (method 4): tR=1.87 min; Mass spectrum (ESI+): m/z=533 [M+H]+.

Aufarbeitung

  1. extractionThe resulting mixture is extracted with ethyl acetate
  2. extractionthe combined extract
  3. washis washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent is evaporated
  6. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30→20:80)
  7. customThe product thus obtained

Quellen und Nachweise

ORD-Eintrag
ord-c81d92de44b44d789f6ffc3c230bc6f6
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08642585B2

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