1-(4-Morpholinocarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine → 3-Acetylthio-1-(4-morpholinocarbonyl-1,3-thiazol-2-yl)azetidine

HRID 891563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891563
[O:1]1[CH2:6][CH2:5][N:4]([C:7]([C:9]2[N:10]=[C:11]([N:14]3[CH2:17][CH:16](OS(C)(=O)=O)[CH2:15]3)[S:12][CH:13]=2)=[O:8])[CH2:3][CH2:2]1.[C:23]([O-:26])(=[S:25])[CH3:24].[K+]>CN(C)C=O>[C:23]([S:25][CH:16]1[CH2:15][N:14]([C:11]2[S:12][CH:13]=[C:9]([C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[O:8])[N:10]=2)[CH2:17]1)(=[O:26])[CH3:24]

Komponenten

4

Edukt 2

HCID 222429461-(4-Morpholinocarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidineHCID 23670855Potassium ethanethioate

Produkt 1

HCID 222427503-Acetylthio-1-(4-morpholinocarbonyl-1,3-thiazol-2-yl)azetidineAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 1-(4-morpholinocarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (680 mg, 1.96 mmol) (obtained as described in Reference Example 11(3)) in dimethylformamide (20 ml) was added potassium thioacetate (671 mg, 5.87 mmol) at room temperature, and then the reaction mixture was stirred in an oil bath (80° C.) for 18 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The obtained organic layer was washed successively 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 n-hexane:ethyl acetate (1:3)→ethyl acetate as the eluant to afford 3-acetylthio-1-(4-morpholinocarbonyl-1,3-thiazol-2-yl)azetidine (411 mg, yield 64%) 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 obtained organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and 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-b4da952b6ae74e03a2a44dc58c2490d0
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001897B2

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