Methyl iodide → 2-(4-{2-[1-(3,4-Dimethyl-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester

HRID 1985238

Reaction equation

HRID 1985238 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[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]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH3:31])[CH:25]=3)[C:20](=[O:32])[NH:19]2)=[CH:11][CH:10]=1)([CH3:7])[CH3:6])[CH3:2].[H-].[Na+].I[CH3:37]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:33])[C:5]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH2:17][CH:18]2[CH2:22][N:21]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH3:31])[CH:25]=3)[C:20](=[O:32])[N:19]2[CH3:37])=[CH:13][CH:14]=1)([CH3:6])[CH3:7])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 577193032-(4-{2-[1-(3,4-Dimethyl-benzyl)-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester

Product 1

HCID 577190842-(4-{2-[1-(3,4-Dimethyl-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl esterYield 74.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(4-{2-[1-(3,4-dimethyl-benzyl)-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester (0.128 g, 0.280 mmol) in DMF (4 mL) was treated with 60% oil suspension of NaH (0.028 g, 0.70 mmol) and stirred at room temperature under N2 for 15 minutes. The reaction was cooled to 0° C. and treated with iodomethane (0.16 g, 1.13 mmol) and then warmed to room temperature and stirred for 1 h. The reaction was quenched with 1 N HCl (3 mL) and worked up extractively with Et2O and water. The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford crude product that was purified by flash chromatography using 5:1 hexanes:acetone to afford 0.098 g (74%) 2-(4-{2-[1-(3,4-dimethyl-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester. MS (ES+) Calc'd for C27H37N2O5 (M+1) 469. Found m/z 469 (100%). 1H NMR.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. temperaturewarmed to room temperature
  3. stirringstirred for 1 h
  4. customThe reaction was quenched with 1 N HCl (3 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customto afford crude product that
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-e46cd8e193b9402a94527a2d55970642
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Linked notes

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