Acetic Acid → HCID 10384705, 화합물

HRID 2184078노트

반응식

HRID 2184078 반응식
[F:1][C:2]([F:18])([F:17])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH3:16])=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[C:19]([O:23][CH2:24][CH3:25])(=[O:22])[CH:20]=[CH2:21].C(O)(=O)C>C(OCC)(=O)C>[OH2:8].[C:3]([OH:8])([C:4]([F:7])([F:6])[F:5])=[O:22].[CH3:16][N:15]([C:12]1[CH:13]=[CH:14][C:9]([C:3]([OH:8])([C:4]([F:6])([F:5])[F:7])[C:2]([F:17])([F:18])[F:1])=[CH:10][CH:11]=1)[CH2:21][CH2:20][C:19]([O:23][CH2:24][CH3:25])=[O:22]

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 8821Ethyl AcrylateHCID 8050151,1,1,3,3,3-Hexafluoro-2-(4-(methylamino)phenyl)propan-2-OL

생성물 2

HCID 10384705HCID 10384705, 화합물수율 73%HCID 22392675Trifluoroacetic acid water

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To the product of step 1 (1.26 g, 4.6 mmol) was added ethyl acrylate (0.55 mL, 5.1 mL) and glacial acetic acid (0.02 mL, 0.3 mmol). After heating the reaction mixture at reflux over 18 h, the solution was cooled to room temperature and diluted with ethyl acetate. The organics were washed several times with water, dried (Na2SO4), and concentrated in vacuo. Purification by reverse phase HPLC using a gradient elution of 60:40 H2O/TFA:CH3CN to 0:100 H2O/TFA:CH3CN at 254 nm afforded the title compound as a white solid (1.25 g, 73%): mp=77° C. 1H NMR (CDCl3) δ 7.49 (d, 2H), 6.78 (d, 2H), 4.06 (q, 2H), 3.63 (t, 2H), 3.26 (br s, 1H), 2.92 (s, 3H), 2.54 (t, 2H), 1.14 (t, 3H). MS (ES+) m/z 374 (MH+). Anal. Calc. for C15H17NO3F6: C, 48.26; H, 4.59; N, 3.75. Found: C, 47.95; H, 4.67; N, 3.73.

후처리

  1. temperatureAfter heating the reaction mixture
  2. temperatureat reflux over 18 h
  3. washThe organics were washed several times with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by reverse phase HPLC
  7. washa gradient elution of 60:40 H2O/TFA

출처 및 근거

ORD 기록
ord-08827fa5fcaf49df970dbe3965c63dd7
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900244B2

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