Trifluoroacetic acid → 2-Methyl-2-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenoxy}-propionic acid ethyl ester

HRID 1985231Notes

Reaction equation

HRID 1985231 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH:18]2[CH2:22][N:21](CC3C=CC(OC)=CC=3)[C:20](=[O:32])[N:19]2[CH3:33])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])[CH3:2].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>O>[CH2:1]([O:3][C:4](=[O:34])[C:5]([CH3:7])([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH2:17][CH:18]2[CH2:22][NH:21][C:20](=[O:32])[N:19]2[CH3:33])=[CH:13][CH:14]=1)[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 577188992-(4-{2-[1-(4-Methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester

Product 1

HCID 577191912-Methyl-2-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenoxy}-propionic acid ethyl esterYield 118.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(4-{2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester (2.72 g, 5.78 mmol) and triethylsilane (1.34 g, 11.5 mmol) was treated with trifluoroacetic acid (70 mL) and stirred at room temperature under N2 for 5 h. The reaction mixture was diluted with water and then extracted with ethyl acetate. The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford crude product that was purified by flash chromatography using 98:2 CH2Cl2:MeOH to afford 2.40 g (100%) 2-methyl-2-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenoxy}-propionic acid ethyl ester. Rf=0.09 (1:1 hexanes:acetone); MS (ES+) Calc'd for C18H27N2O5 (M+1) 351. Found m/z 351 (100%). 1H NMR.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customto afford crude product that
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-76efff47842f424f9d1e32289657f062
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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