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

HRID 891609노트

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HRID 891609 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-83123b2221d0443689bb5f923a0df2fd
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001897B2

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