1-(4-Allyloxycarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine → HCID 22242905, Verbindung

HRID 891683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891683
[CH2:1]([O:4][C:5]([C:7]1[N:8]=[C:9]([N:12]2[CH2:15][CH:14](OS(C)(=O)=O)[CH2:13]2)[S:10][CH:11]=1)=[O:6])[CH:2]=[CH2:3].[C:21]([O-:24])(=[S:23])[CH3:22].[K+]>CN(C)C=O>[C:21]([S:23][CH:14]1[CH2:13][N:12]([C:9]2[S:10][CH:11]=[C:7]([C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[N:8]=2)[CH2:15]1)(=[O:24])[CH3:22]

Komponenten

4

Edukt 2

HCID 222429401-(4-Allyloxycarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidineHCID 23670855Potassium ethanethioate

Produkt 1

HCID 22242905HCID 22242905, VerbindungAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 1-(4-allyloxycarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (2.70 g, 8.51 mmol) (obtained as described in Reference Example 41(3)) in dimethylformamide (135 ml) was added potassium thioacetate (5.83 g, 51.1 mmol) at room temperature. The mixture was stirred in an oil bath (80° C.) for 10 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (2:1) as the eluant to afford 3-acetylthio-1-(4-allyloxycarbonyl-1,3-thiazol-2-yl)azetidine (1.61 g, yield 63%) as a pale brown solid.

Aufarbeitung

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-feef3a46e6f243c999c546b823ba711e
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001897B2

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