3-Methanesulfonyloxy-1-(4-piperidinocarbonyl-1,3-thiazol-2-yl)azetidine → 3-Acetylthio-1-(4-piperidinocarbonyl-1,3-thiazol-2-yl)azetidine

HRID 891609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891609
CS(O[CH:6]1[CH2:9][N:8]([C:10]2[S:11][CH:12]=[C:13]([C:15]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:16])[N:14]=2)[CH2:7]1)(=O)=O.[C:23]([O-:26])(=[S:25])[CH3:24].[K+]>CN(C)C=O>[C:23]([S:25][CH:6]1[CH2:7][N:8]([C:10]2[S:11][CH:12]=[C:13]([C:15]([N:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)=[O:16])[N:14]=2)[CH2:9]1)(=[O:26])[CH3:24]

Komponenten

4

Edukt 2

HCID 222428203-Methanesulfonyloxy-1-(4-piperidinocarbonyl-1,3-thiazol-2-yl)azetidineHCID 23670855Potassium ethanethioate

Produkt 1

HCID 222427853-Acetylthio-1-(4-piperidinocarbonyl-1,3-thiazol-2-yl)azetidineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 3-methanesulfonyloxy-1-(4-piperidinocarbonyl-1,3-thiazol-2-yl)azetidine (346 mg, 1.00 mmol) (obtained as described in Reference Example 27(3)) in dimethylformamide (15 ml) was added potassium thioacetate (687 g, 6.01 mmol) at room temperature. The reaction mixture was stirred in an oil bath (90° C.) for 4 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 ethyl acetate as the eluant to afford 3-acetylthio-1-(4-piperidinocarbonyl-1,3-thiazol-2-yl)azetidine (276 mg, yield 85%) 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-83123b2221d0443689bb5f923a0df2fd
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001897B2

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