1-(4-Cyano-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine → 3-Acetylthio-1-(4-cyano-1,3-thiazol-2-yl)azetidine

HRID 891559노트

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HRID 891559 반응식
[C:1]([C:3]1[N:4]=[C:5]([N:8]2[CH2:11][CH:10](OS(C)(=O)=O)[CH2:9]2)[S:6][CH:7]=1)#[N:2].[C:17]([O-:20])(=[S:19])[CH3:18].[K+]>CN(C)C=O>[C:17]([S:19][CH:10]1[CH2:9][N:8]([C:5]2[S:6][CH:7]=[C:3]([C:1]#[N:2])[N:4]=2)[CH2:11]1)(=[O:20])[CH3:18]

참가 물질

4

반응물 2

HCID 222428691-(4-Cyano-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidineHCID 23670855Potassium ethanethioate

생성물 1

HCID 222429723-Acetylthio-1-(4-cyano-1,3-thiazol-2-yl)azetidine수율 75%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 1-(4-cyano-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (1.12 g, 4.32 mmol) (obtained as described in Reference Example 4(3)) in dimethylformamide (56 ml) was added potassium thioacetate (3.89 g, 27.0 mmol) at room temperature. The mixture was stirred in an oil bath (80° C.) for 4 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 magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (2:1) as the eluant to afford 3-acetylthio-1-(4-cyano-1,3-thiazol-2-yl)azetidine (0.767 g, yield 75%) as a pale brown solid.

후처리

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

출처 및 근거

ORD 기록
ord-7636154b1bb844689a3a1973adb8e4fe
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001897B2

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