Triethylsilane → 2-Butoxy-2-methyl-3-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-propionic acid ethyl ester

HRID 1985151Notes

Reaction equation

HRID 1985151 reaction equation
[CH2:1]([O:3][C:4](=[O:38])[C:5]([O:33][CH2:34][CH2:35][CH2:36][CH3:37])([CH3:32])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19](CC3C=CC(OC)=CC=3)[C:18](=[O:30])[N:17]2[CH3:31])=[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:38])[C:5]([O:33][CH2:34][CH2:35][CH2:36][CH3:37])([CH3:32])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][NH:19][C:18](=[O:30])[N:17]2[CH3:31])=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 688706692-Butoxy-3-(4-{2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-propionic acid ethyl ester

Product 1

HCID 688675082-Butoxy-2-methyl-3-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-propionic acid ethyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid (110 mL) is added dropwise to a solution of 2-Butoxy-3-(4-{2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-propionic acid ethyl ester (5.31 g, 10.1 mmol) and triethylsilane (3.22 mL, 20.2 mmol, d=0.728). The reaction mixture is stirred at ambient temperature for 4 h, concentrated in vacuo, and diluted with ethyl acetate. The solution is washed, then dried, concentrated, and purified by flash chromatography to provide the title compound (4.1 g, 100%). 1H NMR (400 MHz, CDCl3): δ 7.09 (d, 2H, J=8.4 Hz), 6.74 (d, 2H, J=8.4 Hz), 5.36 (s, 1H), 4.17-4.07 (m, 2H), 4.02-3.96 (m, 2H), 3.76-3.68 (m, 2H), 3.55 (t, 1H, J=8.8 hz), 3.40-3.31 (m, 2H), 3.20 (t, 1H, J=8.0 Hz), 2.95, 2.91 (ABq, 2H, J=13.6 Hz), 2.76 (s, 3H), 2.24-2.18 (m, 1H), 1.97-1.88 (m, 1H), 1.58-1.51 (m, 2H), 1.41-1.31 (m, 2H), 1.27 (s, 3H), 1.22 (t, 3H, J=7.2 Hz), 0.89 (t, 3H, J=7.2 Hz). Rf=0.44 in 10% CH3OH in CH2Cl2.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. washThe solution is washed
  4. customdried
  5. concentrationconcentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-04ae98cd849d4d6092b7dac3825a9c38
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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