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

HRID 1025439노트

반응식

HRID 1025439 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6a087f98146b4464807a48f237fff9d3
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729068B2

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