Water → (2R,4S)-4-acetylthio-1-allyloxycarbonyl-2-(2-azidoethyl) pyrrolidine

HRID 975698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 975698
CC(C)([O-])C.[K+].[C:7]([OH:10])(=[S:9])[CH3:8].[CH2:11]([O:14][C:15]([N:17]1[CH2:21][C@H:20](OS(C)(=O)=O)[CH2:19][C@H:18]1[CH2:27][CH2:28][N:29]=[N+:30]=[N-:31])=[O:16])[CH:12]=[CH2:13].O>CN(C)C=O.C(OCC)(=O)C>[C:7]([S:9][C@@H:20]1[CH2:21][N:17]([C:15]([O:14][CH2:11][CH:12]=[CH2:13])=[O:16])[C@H:18]([CH2:27][CH2:28][N:29]=[N+:30]=[N-:31])[CH2:19]1)(=[O:10])[CH3:8]

Komponenten

7

Edukt 4

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 54350989(2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-methanesulfonyloxypyrrolidineHCID 178418634HCID 178418634, Verbindung

Produkt 1

HCID 54165923(2R,4S)-4-acetylthio-1-allyloxycarbonyl-2-(2-azidoethyl) pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of potassium t-butoxide (6.99 g) in dimethylformamide (150 ml) was added thioacetic acid (4.45 ml) under ice-cooling. After stirring for 15 minutes, a solution of (2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-methanesulfonyloxypyrrolidine (15.3 g) in dimethylformamide (20 ml) was added to the mixture under ice-cooling. The mixture was warmed to 80° C. and stirred for 4 hours, then cooled to ambient temperature and poured into water and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The combined organic layer was washed with sat. sodium bicarbonate, water (twice) and brine, dried over magnesium sulfate, and evaporated under reduced pressure to give (2R,4S)-4-acetylthio-1-allyloxycarbonyl-2-(2-azidoethyl) pyrrolidine (14.7 g).

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirred for 4 hours
  4. temperaturecooled to ambient temperature
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted twice with ethyl acetate
  7. washThe combined organic layer was washed with sat. sodium bicarbonate, water (twice) and brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-26b19d95bd91486c91895e71949fb07a
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05608056

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