Triethylsilane → HCID 68867329, compound

HRID 1985130Notes

Reaction equation

HRID 1985130 reaction equation
C([SiH](CC)CC)C.[CH2:8]([O:10][C:11](=[O:48])[C:12]([O:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[F:47])([CH3:39])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH:23]2[CH2:27][N:26](CC3C=CC(OC)=CC=3)[C:25](=[O:37])[N:24]2[CH3:38])=[CH:16][CH:15]=1)[CH3:9]>FC(F)(F)C(O)=O>[CH2:8]([O:10][C:11](=[O:48])[C:12]([O:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[F:47])([CH3:39])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH:23]2[CH2:27][NH:26][C:25](=[O:37])[N:24]2[CH3:38])=[CH:16][CH:15]=1)[CH3:9]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 68866820HCID 68866820, compound

Product 1

HCID 68867329HCID 68867329, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid (70 mL) is added dropwise to a solution of triethylsilane (2.5 mL, 15.73 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 (4.44 g, 7.86 mmol). The reaction mixture is stirred 2 h, then concentrated in vacuo. The residue is diluted with ethyl acetate, then washed with a saturated solution of aqueous sodium carbonate, water, and brine. The organic layer is dried and concentrated to provide the title compound (3.5 g, 100%). 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)+. Rf=0.50 in 10% methanol in methylene chloride.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue is diluted with ethyl acetate
  3. washwashed with a saturated solution of aqueous sodium carbonate, water, and brine
  4. customThe organic layer is dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-393c7545f1864f16a7ce0343f77d06bd
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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