HCID 22242733, Verbindung → HCID 22242720, Verbindung

HRID 891710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891710
[C:1]([CH2:3][N:4]([CH:21]([CH3:23])[CH3:22])[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])#[N:2].[C:24]([O-:27])(=[S:26])[CH3:25].[K+]>CN(C)C=O>[C:24]([S:26][CH:14]1[CH2:13][N:12]([C:9]2[S:10][CH:11]=[C:7]([C:5](=[O:6])[N:4]([CH2:3][C:1]#[N:2])[CH:21]([CH3:22])[CH3:23])[N:8]=2)[CH2:15]1)(=[O:27])[CH3:25]

Komponenten

4

Edukt 2

HCID 22242733HCID 22242733, VerbindungHCID 23670855Potassium ethanethioate

Produkt 1

HCID 22242720HCID 22242720, VerbindungAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 1-[4-(N-cyanomethyl-N-isopropyl-carbamoyl)-1,3-thiazol-2-yl]-3-methanesulfonyloxyazetidine (635 mg, 1.77 mmol) (obtained as described in Reference Example 49(5)) in dimethylformamide (19 ml) was added potassium thioacetate (1.21 g, 10.6 mmol) at room temperature, and the reaction mixture was stirred in an oil bath (90° C.) for 3 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 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 obtained residue was purified by chromatography on a silica gel column using hexane:ethyl acetate (1:1)→ethyl acetate as the eluant to afford 3-acetylthio-1-[4-(N-cyanomethyl-N-isopropyl-carbamoyl)-1,3-thiazol-2-yl]azetidine (344 mg, yield 57%) as a pale brown solid.

Aufarbeitung

  1. customat room temperature
  2. customthe completion of the reaction
  3. customthe reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution
  4. washThe organic layer was washed successively 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 obtained residue was purified by chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-baee7b1662d84d23964aac0dfb65bd97
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001897B2

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