Allyl Alcohol → [4-Amino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid allyl ester

HRID 457958노트

반응식

HRID 457958 반응식
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[C:4]([C:13](=[O:24])[NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=2[F:23])[CH:3]=1.[CH2:25](O)[CH:26]=[CH2:27]>OS(O)(=O)=O>[CH2:27]([O:9][C:8](=[O:10])[CH2:7][O:6][C:5]1[CH:11]=[CH:12][C:2]([NH2:1])=[CH:3][C:4]=1[C:13](=[O:24])[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=1[F:23])[CH:26]=[CH2:25]

참가 물질

4

반응물 2

HCID 7858Allyl AlcoholHCID 12968791HCID 12968791, 화합물

생성물 1

HCID 22093473[4-Amino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid allyl ester수율 20%

시약·촉매·용매 1

HCID 1118Sulfuric Acid촉매

실험 절차

[4-Amino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]acetic acid (0.62 g, 1.56 mmol) was dissolved in allyl alcohol (15 mL, 0.1 M). This solution was treated with 7 drops of concentrated H2SO4 and stirred at room temperature for 48 h. The reaction was concentrated, redissolved in ethyl acetate, washed with H2O, saturated aq NaCl (3×), dried over Na2SO4 and filtered. The filtrate was treated with decolorizing charcoal, boiled for 10 minutes, cooled to room temperature, filtered and concentrated. The crude solid was recrystallized from heptane and ethyl acetate to give [4-amino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid allyl ester as a light orange solid (0.13 g, 20%). 1H NMR (DMSO-d6, 300 MHz) δ 8.92 (br t, J=5.4 Hz, 1 H), 7.49–7.80 (m, 4 H), 6.84 (d, J=8.7 Hz, 1 H), 6.63 (br dd, J1=8.7 Hz, J2=2.7 Hz, 1 H), 5.95–5.79 (m, 1 H), 5.29 (br d, J=17.1 Hz, 1 H), 5.19 (br d, J=10.5 Hz, 1 H), 4.91 (br s, 1 H), 4.83 (br s, 2 H), 4.61 (br d, J=5.4 Hz, 1 H).

후처리

  1. concentrationThe reaction was concentrated
  2. dissolutionredissolved in ethyl acetate
  3. washwashed with H2O, saturated aq NaCl (3×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. additionThe filtrate was treated with decolorizing charcoal
  7. waitboiled for 10 minutes
  8. temperaturecooled to room temperature
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude solid was recrystallized from heptane and ethyl acetate

출처 및 근거

ORD 기록
ord-b0f88fd392154ef7bb241747e79355fe
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189749B2

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