Tetrabutylammonium Fluoride → 2-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-cyclopropanecarboxylic Acid Ethyl Ester

HRID 660644

반응식

HRID 660644 반응식
[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][C:18](=[O:20])[N:17](CC[Si](C)(C)C)[S:16]2(=[O:28])=[O:27])=[C:11]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:10]=1)=[O:5])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][C:18](=[O:20])[NH:17][S:16]2(=[O:27])=[O:28])=[C:11]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:10]=1)=[O:5])[CH3:2]

참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 688399182-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-cyclopropanecarboxylic Acid Ethyl Ester

생성물 1

HCID 688434952-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-cyclopropanecarboxylic Acid Ethyl Ester

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

To 2-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-cyclopropanecarboxylic acid ethyl ester (75 mg, 0.14 mmol) in THF (3 mL) is added 1M TBAF in THF (0.21 mL) and the solution is stirred at 60° C. for 2 h. The reaction is cooled to RT and diluted with EtOAc and washed with 1N HCl and brine. The organic layer is dried over MgSO4 and concentrated under reduced pressure to afford the title compound as a yellow oil, which is used in the next step without further purification: (M+H)+=448.

후처리

  1. temperatureThe reaction is cooled to RT
  2. washwashed with 1N HCl and brine
  3. dry with materialThe organic layer is dried over MgSO4
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-45156971354f4dd3b0c217a724f12ccc
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084448B2

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