Hydrochloric Acid → 3-{[5-(Methoxycarbonyl)pyridin-2-yl](propyl)sulfamoyl}benzoic acid

HRID 926050ノート

反応式

HRID 926050 の反応式
[CH2:1]([N:4]([S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([O:26]CC[Si](C)(C)C)=[O:25])[CH:19]=1)(=[O:17])=[O:16])[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][N:6]=1)[CH2:2][CH3:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl>C1COCC1>[CH3:12][O:11][C:9]([C:8]1[CH:13]=[CH:14][C:5]([N:4]([CH2:1][CH2:2][CH3:3])[S:15]([C:18]2[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=2)[C:24]([OH:26])=[O:25])(=[O:16])=[O:17])=[N:6][CH:7]=1)=[O:10]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 71238187Methyl 6-{propyl[(3-{[2-(trimethylsilyl)ethoxy]carbonyl}phenyl)sulfonyl]amino}nicotinate

生成物 1

HCID 712387833-{[5-(Methoxycarbonyl)pyridin-2-yl](propyl)sulfamoyl}benzoic acid収率 79.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mixture of 175 mg of methyl 6-{propyl[(3-{[2-(trimethylsilyl)ethoxy]carbonyl}phenyl)sulfonyl]amino}nicotinate and 5 mL of THF was added dropwise a solution of TBAF in THF (1 M, 0.750 mL), followed by stirring at room temperature for 4 hours. To the reaction mixture was added 0.1 M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure and then dried under reduced pressure to obtain 110 mg of 3-{[5-(methoxycarbonyl)pyridin-2-yl](propyl)sulfamoyl}benzoic acid as a colorless powder.

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customdried under reduced pressure

出典と根拠

ORDレコード
ord-78e8d6c629e14fd980c9e325c38db832
出典データセット
uspto-grants-2016_03
特許番号
US09284295B2

反応ノート

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