Triethylsilane → 2-Methyl-3-(4-{2-[2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid ethyl ester

HRID 1985171Notes

Reaction equation

HRID 1985171 reaction equation
[CH2:1]([O:3][C:4](=[O:50])[C:5]([CH3:49])([O:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)[C:18](=[O:32])[N:17]2CC2C=CC(OC)=CC=2)=[CH:9][CH:8]=1)[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4](=[O:50])[C:5]([CH3:49])([O:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:24][CH:23]=3)[C:18](=[O:32])[NH:17]2)=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 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 ester

Product 1

HCID 688700092-Methyl-3-(4-{2-[2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid (60 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 (3.46 g, 5.0 lmmol) and triethylsilane (1.6 mL, 10.0 mmol, d=0.728). The reaction mixture is stirred at ambient temperature for 2 hours, concentrated, and diluted with ethyl acetate. The solution is washed with a saturated solution of aqueous sodium bicarbonate, water, and brine, then dried over Na2SO4, and concentrated in vacuo to provide the title compound. 1H NMR (400 MHz, CDCl3): δ 7.58 (d, 2H, J=8.2 Hz), 7.38 (d, 2H, J=8.2 Hz), 7.23-7.14 (m, 4H), 6.97 (t, 1H, J=7.4 Hz), 6.82 (d, 2H, J=7.4 Hz), 6.78-(d, 2H, J=7.4 Hz), 4.44, 4.38 (ABq, 2H, J=15.6 Hz), 4.20 (q, 2H, J=7.4 Hz), 4.07-3.99 (m, 2H), 3.96-3.89 (m, 1H), 3.47 (t, 1H, J=8.2 Hz), 3.27, 3.09 (ABq, 2H, J=14.1 Hz), 3.04, 3.02 (ABq, 1H, J=6.7 Hz), 2.08-1.99 (m, 1H), 1.98-1.92 (m, 1H), 1.38 (s, 3H), 1.21 (t, 3H, J=6.7 Hz). MS [EI+] 571 (M+H)+, [EI−] 569 (M−H)+. Rf=0.07 in 33% acetone in hexanes.

Workup

  1. concentrationconcentrated
  2. additiondiluted with ethyl acetate
  3. washThe solution is washed with a saturated solution of aqueous sodium bicarbonate, water, and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a9ed001861a8422ba3d4083f84238d77
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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