Trifluoroacetic acid → HCID 68867329, compound

HRID 1985139Notes

Reaction equation

HRID 1985139 reaction equation
FC(F)(F)C(O)=O.C([SiH](CC)CC)C.[CH2:15]([O:17][C:18](=[O:55])[C:19]([O:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[F:54])([CH3:46])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH:30]2[CH2:34][N:33](CC3C=CC(OC)=CC=3)[C:32](=[O:44])[N:31]2[CH3:45])=[CH:23][CH:22]=1)[CH3:16]>>[CH2:15]([O:17][C:18](=[O:55])[C:19]([O:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[F:54])([CH3:46])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH:30]2[CH2:34][NH:33][C:32](=[O:44])[N:31]2[CH3:45])=[CH:23][CH:22]=1)[CH3:16]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68866820HCID 68866820, compound

Product 1

HCID 68867329HCID 68867329, compoundYield 99.7%

Procedure

Trifluoroacetic acid (55 mL) is added dropwise to a solution of triethylsilane (1.95 mL, 12.18 mmol, d=0.728) and 2-(2-Fluoro-phenoxy)-3-(4-{2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-propionic acid ethyl ester (3.44 g, 6.09 mmol). The reaction mixture is stirred under nitrogen at ambient temperature for 2 h, then concentrated. The residue is diluted with ethyl acetate, then washed. The organic layer is dried and concentrated in vacuo to provide the title compound (2.7 g, 78%). 1H NMR (400 MHz, CDCl3): δ 7.20 (d, 2H, J=8.7 Hz), 7.06-7.01 (m, 1H), 6.97-6.87 (m, 3H), 6.79 (d, 2H, J=8.7 Hz), 5.04-4.98 (m, 1H), 4.20 (q, 2H, J=6.8 Hz), 4.02 (t, 2H, J=6.8 Hz), 3.76-3.69 (m, 1H), 3.55 (t, 1H, J=8.7 Hz), 3.26, 3.14 (ABq, 2H, J=14.5 Hz), 3.21 (t, 1H, J=8.7 Hz), 2.78 (s, 3H), 2.27-2.20 (m, 1H), 1.99-1.90 (m, 1H), 1.38 (s, 3H), 1.23 (t, 3H, J=6.8 Hz), 0.96 (t, 2H, J=7.7 Hz). MS [EI+] 445 (M+H)+.

Workup

  1. concentrationconcentrated
  2. additionThe residue is diluted with ethyl acetate
  3. washwashed
  4. customThe organic layer is dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b6d6c157884e4186a98e27786e21363e
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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