Trifluoroacetic acid → HCID 18468176、化合物

HRID 457946ノート

反応式

HRID 457946 の反応式
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

参加物

5

反応物 2

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

生成物 1

HCID 18468176HCID 18468176、化合物収率 92%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-234e057188b5421eabff4935d0b82d9d
出典データセット
uspto-grants-2007_03
特許番号
US07189749B2

反応ノート

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