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Water → (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-N,N-dimethyl-acetamide

HRID 602764
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HRID 602764 반응식
C(OC([N:8]1[C:20]2[CH2:19][CH:18]([C:21]([S:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)(=[O:29])=[O:28])([F:26])[C:22](=[O:25])[NH:23][CH3:24])[CH2:17][CH2:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([Cl:36])[CH:13]=2)=O)(C)(C)C.[H-].[Na+].[CH3:39]I.O>CN(C=O)C>[C:30]1([S:27]([C:21]([CH:18]2[CH2:17][CH2:16][C:15]3[C:14]4[C:9](=[CH:10][CH:11]=[C:12]([Cl:36])[CH:13]=4)[NH:8][C:20]=3[CH2:19]2)([F:26])[C:22]([N:23]([CH3:39])[CH3:24])=[O:25])(=[O:28])=[O:29])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67267476(RS,SR)-2-(benzenesulfonyl-fluoro-methylcarbamoyl-methyl)-6-chloro-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester

생성물 1

HCID 11328370(RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-N,N-dimethyl-acetamide수율 73.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

680 mg (1.27 mmol) of (RS,SR)-2-(benzenesulfonyl-fluoro-methylcarbamoyl-methyl)-6-chloro-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester in 10 mL of DMF were treated with 83 mg (1.90 mmol, 1.5 eq) of NaH (55% in oil) portionwise within 30 min at 0° C. 217 mg (1.52 mmol, 1.2 eq) of methyliodide were added and the reaction was stirred an additional 30 min, and then poured into water and extracted with EtOAc. The crude material was dissolved in 10 mL of CH2Cl2, and 1 mL of TFA was added at RT. Aqueous Na2CO3 was added until pH=7 was reached, and the organic phases were dried on Na2SO4, filtered and evaporated. Column chromatography on silica gel with heptane/EtOAc 1:1 yielded 420 mg (65%) of (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-N,N-dimethyl-acetamide as a white solid, MS: 449 (MH+).

후처리

  1. extractionextracted with EtOAc
  2. dissolutionThe crude material was dissolved in 10 mL of CH2Cl2
  3. addition1 mL of TFA was added at RT
  4. additionAqueous Na2CO3 was added until pH=7
  5. customthe organic phases were dried on Na2SO4
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-aa55e25ff7434fdca4bc2e11615ccd8e
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07906546B2

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