Acetic Acid → HCID 10384705, compound

HRID 2184078Notes

Reaction equation

HRID 2184078 reaction equation
[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]

Participants

6

Reactant 3

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-08827fa5fcaf49df970dbe3965c63dd7
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

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