Trifluoroacetic acid → HCID 18468176, 화합물

HRID 457946노트

반응식

HRID 457946 반응식
C([O:5][C:6](=[O:30])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[C:18](=[O:29])[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=1[F:28])(C)(C)C.FC(F)(F)C(O)=O>ClCCl.O>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][NH:19][C:18]([C:10]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]([OH:30])=[O:5])=[O:29])=[C:22]([F:28])[CH:23]=1

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 22093497(2-(4-Bromo-2-fluoro-benzylcarbamoyl)-4-nitro-phenoxy]-acetic acid tert-butyl ester

생성물 1

HCID 18468176HCID 18468176, 화합물수율 92%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A solution of (2-(4-bromo-2-fluoro-benzylcarbamoyl)-4-nitro-phenoxy]-acetic acid tert-butyl ester in dichloromethane (11 mL, 0.2 M) was treated with trifluoroacetic acid (3.0 mL, 4.44 g. 39.0 mmol) and stirred for 24 h. The reaction was diluted with H2O and extracted with ethyl acetate (3×). The combined organic extracts were washed with H2O (2×), saturated aq NaCl, dried over MgSO4, filtered and concentrated to a crude solid that was recrystallized from heptane and ethyl acetate to give (2-(4-bromo-2-fluoro-benzylcarbamoyl)-4-nitro-phenoxy]-acetic acid as a white crystalline solid (0.98 g, 92%); Rf 0.10 (10% ethyl acetate in dichloromethane); 1H NMR (DMSO-d6, 300 MHz) δ 9.14 (br t, J=6.0 Hz, 1 H), 8.58 (d, J=3.3 Hz, 1 H), 8.34 (dd, J1=9.0 Hz, J2=3.0 Hz, 1 H), 7.52 (br dd, J, =9.3 Hz, J2=3.0 Hz, 1 H), 7.43–7.32 (m, 3 H), 5.02 (s, 2 H), 4.52 (d, J=6.0 Hz, 2H). ESI-LC/MS m/z calcd for C16H12BrFN2O6: 426.0 found 427.0 (M+1)+. Anal. calcd for C16H12BrFN2O6: C, 44.99; H, 2.83; N, 6.56. Found C, 44.97; H, 2.83; N, 6.47.

후처리

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with H2O (2×), saturated aq NaCl
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a crude solid that
  6. customwas recrystallized from heptane and ethyl acetate

출처 및 근거

ORD 기록
ord-234e057188b5421eabff4935d0b82d9d
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189749B2

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