Potassium Carbonate → (2R,3S)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-5-(3'-fluoro-4'-methylbiphenyl-4-yl)-3-hydroxypentanoic acid

HRID 84034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 84034
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C@H:14]([C@@H:18]([O:35]C=O)[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([F:34])[CH:28]=2)=[CH:23][CH:22]=1)[C:15]([OH:17])=[O:16].C(=O)([O-])[O-].[K+].[K+].S([O-])(O)(=O)=O.[Na+]>CO.C(OCC)(=O)C>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C@H:14]([C@@H:18]([OH:35])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([F:34])[CH:28]=2)=[CH:23][CH:22]=1)[C:15]([OH:17])=[O:16]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 516919Sodium BisulfateHCID 86700979(2R,3S)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-5-(3'-fluoro-4'-methylbiphenyl-4-yl)-3-(formyloxy)pentanoic acid

Produkt 1

HCID 25009401(2R,3S)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-5-(3'-fluoro-4'-methylbiphenyl-4-yl)-3-hydroxypentanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of the compound obtained from step o above (0.31 g) in methanol (5 mL), potassium carbonate (0.094 g) was added at 0° C. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate (50 mL), acidified with sodium hydrogen sulphate, and washed with water (20 mL). The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain a residue which was purified by preparative thin layer chromatography using 10% methanol in dichloromethane as eluant to afford the title compound (0.020 g).

Aufarbeitung

  1. washwashed with water (20 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customto obtain a residue which
  5. customwas purified by preparative thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fe79c073a1de45b6a2519c02a71dc776
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846910B2

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