Hydrochloric Acid → 7-[methyl(2-thienylsulfonyl)amino]-5-(trifluoromethoxy)-1H-indole-2-carboxylic acid

HRID 1851562ノート

反応式

HRID 1851562 の反応式
COC[N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:10][C:11]=2[N:13]([CH3:22])[S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])[CH:6]=[C:5]1[C:28]([O:30]CC)=[O:29].Cl.O1CCCC1>C(O)C>[CH3:22][N:13]([S:14]([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)(=[O:15])=[O:16])[C:11]1[CH:10]=[C:9]([O:23][C:24]([F:26])([F:27])[F:25])[CH:8]=[C:7]2[C:12]=1[NH:4][C:5]([C:28]([OH:30])=[O:29])=[CH:6]2

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 57901767Ethyl 1-(methoxymethyl)-7-[methyl(2-thienylsulfonyl)amino]-5-(trifluoromethoxy)-1H-indole-2-carboxylate

生成物 1

HCID 574761867-[methyl(2-thienylsulfonyl)amino]-5-(trifluoromethoxy)-1H-indole-2-carboxylic acid収率 101.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixed solution of ethyl 1-(methoxymethyl)-7-[methyl(2-thienylsulfonyl)amino]-5-(trifluoromethoxy)-1H-indole-2-carboxylate (0.75 g), 6N hydrochloric acid (15 mL), tetrahydrofuran (4 mL) and ethanol (16 mL) was stirred at 80° C. for 18 hr. The reaction solution was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained colorless solid was dissolved in a mixed solution of tetrahydrofuran (10 mL) and methanol (10 mL). aqueous solution (5 mL) of 85% potassium hydroxide (0.35 g) was added, and the mixture was stirred at room temperature for 18 hr. Aqueous citric acid solution was added to the reaction solution, and the mixture was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (0.65 g, yield 100%) as pale-pink crystals. The obtained crystals were washed with ethyl acetate-hexane to give colorless prism crystals. MS:421 (MH+). melting point 245-246° C.

後処理

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionThe obtained residue was diluted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe obtained colorless solid was dissolved in a mixed solution of tetrahydrofuran (10 mL) and methanol (10 mL)
  7. additionaqueous solution (5 mL) of 85% potassium hydroxide (0.35 g) was added
  8. additionAqueous citric acid solution was added to the reaction solution
  9. extractionthe mixture was extracted with ethyl acetate
  10. washwashed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-6e9a500b104841058cb3dd433175c8e6
出典データセット
uspto-grants-2015_02
特許番号
US08957070B2

反応ノート

読み込み中…