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Tetrahydrofuran → 4-(5-Chloro-3-methyl-benzo[b]thiophene-2-sulfonylamino)-3-methanesulfonyl-benzoic acid methyl ester

HRID 1790219
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HRID 1790219 반응식
C1COCC1.[NH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=1[S:17]([CH3:20])(=[O:19])=[O:18].[H-].[Na+].[Cl:23][C:24]1[CH:37]=[CH:36][C:27]2[S:28][C:29]([S:32](Cl)(=[O:34])=[O:33])=[C:30]([CH3:31])[C:26]=2[CH:25]=1>CN(C=O)C>[Cl:23][C:24]1[CH:37]=[CH:36][C:27]2[S:28][C:29]([S:32]([NH:6][C:7]3[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=3[S:17]([CH3:20])(=[O:19])=[O:18])(=[O:33])=[O:34])=[C:30]([CH3:31])[C:26]=2[CH:25]=1
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참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydride2회HCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chlorideHCID 22041468methyl 4-Amino-3-methylsulfonylbenzoate

생성물 1

HCID 101624624-(5-Chloro-3-methyl-benzo[b]thiophene-2-sulfonylamino)-3-methanesulfonyl-benzoic acid methyl ester수율 44.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Into a mixed solvent of 20 mL of THF and 3 mL of DMF was dissolved 985 mg of methyl 4-amino-3-methanesulfonylbenzoate, followed by addition of 170 mg of sodium hydride (oily, 60%) at 0° C. After 20 minutes of stirring at the same temperature, 1.28 g of 5-chloro-2-chlorosulfonyl-3-methylbenzo[b]thiophene was added at 0° C., followed by 1 hour of stirring at room temperature. Further, 150 mg of sodium hydride (oily, 60%) was added at room temperature and the mixture was stirred for 2 hours at the same temperature. After confirmation of disappearance of the starting material, the reaction was terminated by adding saturated aqueous ammonium chloride solution at 0° C., followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=3/1) to obtain 911 mg of the title compound as colorless powder.

후처리

  1. additionwas added at 0° C.
  2. stirringthe mixture was stirred for 2 hours at the same temperature
  3. customAfter confirmation of disappearance of the starting material, the reaction was terminated
  4. additionby adding saturated aqueous ammonium chloride solution at 0° C.
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed by evaporation
  9. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=3/1)

출처 및 근거

ORD 기록
ord-c68c8c1c71e8490ca4bfbc32fb5643b0
출처 데이터셋
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07071220B2

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