Trifluoroacetic acid → HCID 68868812, compound

HRID 1985167Notes

Reaction equation

HRID 1985167 reaction equation
C(OC(=O)C(OC1C=CC(C2C=CC=CC=2OCCC2CN(CC3C=CC(C(F)(F)F)=CC=3)C(=O)N2)=CC=1)C)C.FC(F)(F)C(O)=O.C([O:50][C:51](=[O:97])[C:52]([CH3:96])([O:89][C:90]1[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=1)[CH2:53][C:54]1[CH:59]=[CH:58][C:57]([O:60][CH2:61][CH2:62][CH:63]2[CH2:67][N:66]([CH2:68][C:69]3[CH:74]=[CH:73][C:72]([C:75]([F:78])([F:77])[F:76])=[CH:71][CH:70]=3)[C:65](=[O:79])[N:64]2[CH2:80][C:81]2C=CC(OC)=CC=2)=[CH:56][CH:55]=1)C.C([SiH](CC)CC)C>>[CH2:80]([N:64]1[CH:63]([CH2:62][CH2:61][O:60][C:57]2[CH:58]=[CH:59][C:54]([CH2:53][C:52]([CH3:96])([O:89][C:90]3[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=3)[C:51]([OH:97])=[O:50])=[CH:55][CH:56]=2)[CH2:67][N:66]([CH2:68][C:69]2[CH:74]=[CH:73][C:72]([C:75]([F:76])([F:78])[F:77])=[CH:71][CH:70]=2)[C:65]1=[O:79])[CH3:81]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 688698823-(4-{2-[3-(4-Methoxy-benzyl)-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-2-phenoxy-propionic acid ethyl esterHCID 86760878HCID 86760878, compound

Product 1

HCID 68868812HCID 68868812, compound

Procedure

2-Methyl-3-(4-{2-[2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl -ethoxy]-phenyl}-2-phenoxy-propionic acid ethyl ester: Trifluoroacetic acid (66 mL) is added dropwise to a solution of 3-(4-{2-[3-(4-Methoxy-benzyl)-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester (3.80 g, 5.50 mmol) and triethylsilane (1.76 mL, 11.0 mmol, d=0.728). The reaction mixture is stirred at ambient temperature for 4 hours, concentrated in vacuo, and diluted with ethyl acetate. The solution is washed, then dried, and concentrated to provide the title compound. 1H NMR (400 MHz, CDCl3): δ 7.58 (d, 2H, J=7.7 Hz), 7.38 (d, 2H, J=7.7 Hz), 7.22 (t, 2H, J=9.1 Hz), 7.15 (d, 2H, J=9.1 Hz), 6.97 (t, 1H, J=7.7 Hz), 6.82 (d, 2H, J=7.7 Hz), 6.78 (d, 2H, J=9.1 Hz), 4.41 (q, 2H, J=14.8 Hz), 4.22, 4.18 (ABq, 2H, J=7.0 Hz), 4.04-4.01 (m, 2H), 3.97-3.90 (m, 1H), 3.43 (t, 1H, J=8.4 Hz), 3.26, 3.10 (ABq, 2H, J=14.1 Hz), 3.04, 3.02 (ABq, 1H, J=7.0 Hz), 2.08-1.99 (m, 1H), 1.98-1.90 (m, 1H), 1.38 (s, 3H), 1.21 (t, 3H, J=7.0 Hz). MS [EI+] 571 (M+H)+, [EI−] 569 (M−H)+. Rf=0.17 in 33% acetone in hexanes.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. washThe solution is washed
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3577cc3396a64f549bbadd6c1cf19535
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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