1-[4-(Furan-2-carbonylamino)methyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine → 3-Acetylthio-1-[4-(furan-2-carbonylamino)methyl-1,3-thiazol-2-yl]azetidine

HRID 891790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891790
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][CH2:9][C:10]1[N:11]=[C:12]([N:15]2[CH2:18][CH:17](OS(C)(=O)=O)[CH2:16]2)[S:13][CH:14]=1)=[O:7].[C:24]([O-:27])(=[S:26])[CH3:25].[K+]>CN(C)C=O>[C:24]([S:26][CH:17]1[CH2:16][N:15]([C:12]2[S:13][CH:14]=[C:10]([CH2:9][NH:8][C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[O:7])[N:11]=2)[CH2:18]1)(=[O:27])[CH3:25]

Komponenten

4

Edukt 2

HCID 222428961-[4-(Furan-2-carbonylamino)methyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidineHCID 23670855Potassium ethanethioate

Produkt 1

HCID 222429283-Acetylthio-1-[4-(furan-2-carbonylamino)methyl-1,3-thiazol-2-yl]azetidineAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 1-[4-(furan-2-carbonylamino)methyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (481 mg, 1.34 mmol) (obtained as described in Reference Example 67(3)) in dimethylformamide (14 ml) was added potassium thioacetate (921 mg, 8.07 mmol) at room temperature and the mixture was stirred in an oil bath (90° C.) for 6 hours. After checking the completion of the reaction, the mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and 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 hexane:ethyl acetate (1:1) as the eluant to afford 3-acetylthio-1-[4-(furan-2-carbonylamino)methyl-1,3-thiazol-2-yl]azetidine (341 mg, yield 83%) as a pale brown solid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-bcf5e074f20141098224940648d37f9f
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001897B2

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