Trimethylsilyl triflate → Ethyl 3-acetylamino-9-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-1,5-dioxaspiro[5.5]undec-7-ene-8-carboxylate

HRID 2191156ノート

反応式

HRID 2191156 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][C:16]([O:26][CH3:27])([O:24][CH3:25])[CH2:15][CH2:14]1)(=[O:12])=[O:11].OC[CH:30]([NH:33][C:34](=[O:36])[CH3:35])CO.C(O[Si](C)(C)C)(C)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C(=O)([O-])O.[Na+]>ClCCl>[C:34]([NH:33][CH:30]1[CH2:25][O:24][C:16]2([CH2:15][CH2:14][CH:13]([S:10](=[O:11])(=[O:12])[NH:9][C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[Cl:1])[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17]2)[O:26][CH2:27]1)(=[O:36])[CH3:35]

参加物

7

反応物 5

HCID 65367Trimethylsilyl triflateHCID 74578Trimethyl(1-methylethoxy)silaneHCID 516892Sodium BicarbonateHCID 11804802N-(1,3-dihydroxypropan-2-yl)acetamideHCID 67192731Ethyl 6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-3,3-dimethoxy-1-cyclohexene-1-carboxylate

生成物 1

HCID 16659748Ethyl 3-acetylamino-9-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-1,5-dioxaspiro[5.5]undec-7-ene-8-carboxylate収率 50%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

500 mg (1.19 mmol) of ethyl 6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-3,3-dimethoxy-1-cyclohexene-1-carboxylate obtained in Example (16a) and 205 mg (1.54 mmol) of N-(2-hydroxy-1-hydroxymethylethyl)acetamide were dissolved in 20 ml of dichloromethane, and 0.84 ml (4.74 mmol) of isopropoxytrimethylsilane and 43 μl (0.24 mmol) of trimethylsilyl trifluoromethanesulfonate were added sequentially with stirring under ice-cooling, followed by stirring for 30 minutes at the same temperature, and further for 66 hours at room temperature. Saturated aqueous sodium hydrogencarbonate was added to the reaction solution and the mixture was extracted with dichloromethane. 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; ethyl acetate methanol=39:1) to give 288 mg of the title compound as an amorphous substance (yield: 50%).

後処理

  1. temperaturecooling
  2. stirringby stirring for 30 minutes at the same temperature
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationfollowed by concentration under reduced pressure

出典と根拠

ORDレコード
ord-1003d54a78bf435ab3b8a5b85154b4a5
出典データセット
uspto-grants-2012_12
特許番号
USRE043858E1

反応ノート

読み込み中…