1,4-Butanediol → Ethyl 3-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-7,12-dioxaspiro[5.6]dodec-1-ene-2-carboxylate

HRID 2191164노트

반응식

HRID 2191164 반응식
[CH2:1](O)[CH2:2]CCO.C(O[Si](C)(C)C)(C)C.[Cl:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[NH:23][S:24]([CH:27]1[C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31][C:30]([O:40][CH3:41])([O:38][CH3:39])[CH2:29][CH2:28]1)(=[O:26])=[O:25].FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C(=O)([O-])O.[Na+]>ClCCl>[Cl:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[NH:23][S:24]([CH:27]1[CH2:28][CH2:29][C:30]2([O:38][CH2:39][CH2:2][CH2:1][CH2:41][O:40]2)[CH:31]=[C:32]1[C:33]([O:35][CH2:36][CH3:37])=[O:34])(=[O:25])=[O:26]

참가 물질

7

반응물 5

HCID 80641,4-ButanediolHCID 65367Trimethylsilyl triflateHCID 74578Trimethyl(1-methylethoxy)silaneHCID 516892Sodium BicarbonateHCID 67192731Ethyl 6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-3,3-dimethoxy-1-cyclohexene-1-carboxylate

생성물 1

HCID 57870969Ethyl 3-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-7,12-dioxaspiro[5.6]dodec-1-ene-2-carboxylate수율 3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

34 mg (0.61 mmol) of 1,4-butanediol was dissolved in 5 ml of dichloromethane, 0.32 ml (1.83 mmol) of isopropoxytrimethylsilane, and 200 mg (0.47 mmol) of ethyl 6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-3,3-dimethoxy-1-cyclohexene-1-carboxylate obtained in Example (16a) and 4 μl (0.024 mmol) of trimethylsilyl trifluoromethanesulfonate were sequentially added thereto with stirring under ice-cooling, followed by stirring for 2 hours at the same temperature. Saturated aqueous sodium hydrogencarbonate was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was subjected to silica gel column chromatography (solvent; hexane:ethyl acetate=3:1), and the resulting solid was further washed with hexane to give 6 mg of the title compound as a white powder (yield: 3%).

후처리

  1. temperaturecooling
  2. stirringby stirring for 2 hours at the same temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationfollowed by concentration under reduced pressure
  7. washthe resulting solid was further washed with hexane

출처 및 근거

ORD 기록
ord-2e134733c4294b8d952611a9e4548ce8
출처 데이터셋
uspto-grants-2012_12
특허 번호
USRE043858E1

반응 노트

불러오는 중…