Hydrochloric Acid → 3-{Ethyl[4-(methoxycarbonyl)phenyl]sulfamoyl}benzoic acid

HRID 1025437ノート

反応式

HRID 1025437 の反応式
[CH2:1]([N:3]([C:22]1[CH:27]=[CH:26][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=1)[S:4]([C:7]1[CH:8]=[C:9]([CH:19]=[CH:20][CH:21]=1)[C:10]([O:12]CC[Si](C)(C)C)=[O:11])(=[O:6])=[O:5])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl>C1COCC1>[CH2:1]([N:3]([C:22]1[CH:23]=[CH:24][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:27]=1)[S:4]([C:7]1[CH:8]=[C:9]([CH:19]=[CH:20][CH:21]=1)[C:10]([OH:12])=[O:11])(=[O:6])=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 712385732-(Trimethylsilyl)ethyl 3-{ethyl[4-(methoxycarbonyl)phenyl]sulfamoyl}benzoate

生成物 1

HCID 712384373-{Ethyl[4-(methoxycarbonyl)phenyl]sulfamoyl}benzoic acid収率 92%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mixture of 330 mg of 2-(trimethylsilyl)ethyl 3-{ethyl[4-(methoxycarbonyl)phenyl]sulfamoyl}benzoate and 5.0 mL of THF was added a solution of TBAF in THF (1.0 M, 1.42 mL), followed by stirring at room temperature for 15 hours. To the reaction mixture was added a 0.1 M aqueous hydrochloric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with a 0.1 M aqueous hydrochloric acid solution and a 10% aqueous citric acid solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 238 mg of 3-{ethyl[4-(methoxycarbonyl)phenyl]sulfamoyl}benzoic acid as a white solid.

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a 0.1 M aqueous hydrochloric acid solution
  3. dry with materiala 10% aqueous citric acid solution, and dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-40afef8da777431caf8dd861802a2a4c
出典データセット
uspto-grants-2014_05
特許番号
US08729068B2

反応ノート

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