Trimethylsilyl iodide → N-[(4aR,7aS)-7a-Phenyl-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

HRID 1619039노트

반응식

HRID 1619039 반응식
I[Si](C)(C)C.[C:6]([NH:14][C:15]1[S:16][CH2:17][C@@H:18]2[CH2:23][N:22](C(OCC3C=CC=CC=3)=O)[CH2:21][C@:19]2([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:20]=1)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(#N)C>[C:34]1([C@:19]23[CH2:21][NH:22][CH2:23][C@H:18]2[CH2:17][S:16][C:15]([NH:14][C:6](=[O:13])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:20]3)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

참가 물질

4

반응물 2

HCID 85247Trimethylsilyl iodideHCID 86762230benzyl (4aR,7aS)-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

생성물 1

HCID 86762229N-[(4aR,7aS)-7a-Phenyl-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide수율 399.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Iodotrimethylsilane (10 mL, 70 mmol) is added to a solution of benzyl (4aR,7aS)-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate (11 g, 23 mmol) in acetonitrile (165 mL), stirred at room temperature for 2 hours and concentrated. The mixture is diluted with water (100 mL) and ethyl acetate (150 mL) and the pH adjusted to 4 with 1 M hydrochloric acid. The aqueous layer is collected. The pH of this aqueous layer is then adjusted to 10 with 2 M sodium hydroxide. The resulting solution is then extracted with ethyl acetate (100 mL), dried over magnesium sulfate and concentrated to give the title compound (31 g, 63%). ES/MS (m/e): 338 (M+H).

후처리

  1. concentrationconcentrated
  2. additionThe mixture is diluted with water (100 mL) and ethyl acetate (150 mL)
  3. customThe aqueous layer is collected
  4. extractionThe resulting solution is then extracted with ethyl acetate (100 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0f226877e19242eeac188ecdf2c5948c
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772282B2

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