Reaktion #978771

Reaktionsgleichung

(3S)-1-(4-carbamoyl-1,3-thiazol-2-yl)-3-methanesulfonyloxypyrrolidine

potassium thioacetate

→

(3R)-3-acetylthio-1-(4-carbamoyl-1,3-thiazol-2-yl)pyrrolidine

Ausbeute 90.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturunder reflux for 6 hours
3. 3
   Sonstigethe completion of the reaction
4. 4
   Sonstigethe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
5. 5
   WaschenThe organic layer was washed with saturated aqueous sodium chloride solution
6. 6
   Trocknendried over anhydrous sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   SonstigeThe residue was purified by chromatography on a silica gel column

Vorschrift

To a solution of (3S)-1-(4-carbamoyl-1,3-thiazol-2-yl)-3-methanesulfonyloxypyrrolidine (1.15 g) (obtained as described in Reference Example 20(8)) in acetonitrile (35 ml) was added potassium thioacetate (1.35 g, 11.8 mmol) at room temperature, and the mixture was heated under reflux for 6 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate 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 ethyl acetate→2% methanol in ethyl acetate as the eluant to afford (3R)-3-acetylthio-1-(4-carbamoyl-1,3-thiazol-2-yl)pyrrolidine (962 mg, yield 90%) as a pale brown solid.

Quelle