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Hydrochloric Acid → (2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(1R)-3-oxocyclopentyl]propanoic acid

HRID 2192910
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2192910
[CH:1]1([C:4]2[CH:5]=[C:6]([C@@H:16]([CH2:20][C@H:21]3[CH2:25][CH2:24][C:23]4(OCC(C)(C)C[O:26]4)[CH2:22]3)[C:17]([OH:19])=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH2:3][CH2:2]1.Cl>CC(C)=O>[CH:1]1([C:4]2[CH:5]=[C:6]([C@@H:16]([CH2:20][C@H:21]3[CH2:25][CH2:24][C:23](=[O:26])[CH2:22]3)[C:17]([OH:19])=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:14][CH2:15]2)(=[O:12])=[O:11])[CH2:2][CH2:3]1
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Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 59570883(2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(2R)-8,8-dimethyl-6,10-dioxaspiro[4.5]dec-2-yl]propionic acid

Produkt 1

HCID 59570882(2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(1R)-3-oxocyclopentyl]propanoic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of (2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(2R)-8,8-dimethyl-6,10-dioxaspiro[4.5]dec-2-yl]propionic acid (22 g), 4 M hydrochloric acid (22 mL), and acetone (88 mL) was stirred under heating and reflux for 2 hours. The solvent was evaporated under reduced pressure, and then to the residue were added ethyl acetate/water (1/3, 300 mL) and sodium hydroxide (5.7 g) under ice-cooling. To the aqueous layer was added concentrated hydrochloric acid under ice-cooling to adjust the pH to 1, and chloroform was added thereto. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was then evaporated under reduced pressure to obtain (2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(1R)-3-oxocyclopentyl]propionic acid (17.9 g) as a colorless amorphous substance.

Aufarbeitung

  1. temperatureunder heating
  2. temperaturereflux for 2 hours
  3. customThe solvent was evaporated under reduced pressure
  4. additionto the residue were added ethyl acetate/water (1/3, 300 mL) and sodium hydroxide (5.7 g) under ice-
  5. temperaturecooling
  6. additionTo the aqueous layer was added concentrated hydrochloric acid under ice-
  7. temperaturecooling
  8. additionwas added
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. customthe solvent was then evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-967753dac5dd464e87dceec43f930c7a
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08329707B2

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