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

HRID 1527227노트

반응식

HRID 1527227 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c12e82a023754fca90ec877ffd1c368f
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085555B2

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