Trifluoroacetic acid → (3-Acetyl-5-trifluoromethoxy-indol-1-yl)acetic acid

HRID 1527227ノート

反応式

HRID 1527227 の反応式
C([O:5][C:6](=[O:25])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:14][CH:15]=2)[C:10]([C:22](=[O:24])[CH3:23])=[CH:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO>[C:22]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:20])([F:21])[F:19])[CH:12]=2)[N:8]([CH2:7][C:6]([OH:25])=[O:5])[CH:9]=1)(=[O:24])[CH3:23]

参加物

5

反応物 2

HCID 6422Trifluoroacetic acidHCID 68284069(3-Acetyl-5-trifluoromethoxy-indol-1-yl)-acetic acid tert-butyl ester

生成物 1

HCID 68284505(3-Acetyl-5-trifluoromethoxy-indol-1-yl)acetic acid

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (3-acetyl-5-trifluoromethoxy-indol-1-yl)-acetic acid tert-butyl ester (680 mg, 1.90 mmol) in CH2Cl2 (10 mL) was added TFA (1.47 mL, 19.0 mmol), and stirring was continued at RT overnight. The reaction mixture was then diluted with CH2Cl2 and MeOH, and volatiles were evaporated under reduced pressure. The residue was taken up in MeOH and then evaporated again. The crude material was taken up in 1M aqueous NaOH solution (5 mL), and the water layer was washed with CH2Cl2 and subsequently acidified to pH=1 by addition of a 6M HCl solution. The precipitate was filtered and dried at 50° C. in vacuo for 1 h to afford the title compound as a off-white solid: MS: 302.0 [M+H]+; tR (HPLC conditions c): 4.40 min. The material thus obtained was used directly in the next step without further purification.

後処理

  1. customwere evaporated under reduced pressure
  2. customevaporated again
  3. washthe water layer was washed with CH2Cl2
  4. additionsubsequently acidified to pH=1 by addition of a 6M HCl solution
  5. filtrationThe precipitate was filtered
  6. customdried at 50° C. in vacuo for 1 h

出典と根拠

ORDレコード
ord-c12e82a023754fca90ec877ffd1c368f
出典データセット
uspto-grants-2015_07
特許番号
US09085555B2

反応ノート

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