Methyl iodide → [1-(4-Methoxy-benzyl)-3-methyl-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl ester

HRID 1985116Notes

Reaction equation

HRID 1985116 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH:5]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:7](=[O:20])[NH:6]1.[H-].[Na+].[CH3:24]I>CN(C=O)C>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH:5]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:7](=[O:20])[N:6]1[CH3:24]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57718915[1-(4-Methoxy-benzyl)-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl ester

Product 1

HCID 57719141[1-(4-Methoxy-benzyl)-3-methyl-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 0° C. solution of compound [1-(4-methoxy-benzyl)-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl ester (9.84 g, 33.7 mmol) in DMF (30 mL) was treated with sodium hydride (60% dispersion, 1.37 g, 34.3 mmol) and warmed to room temperature and stirred under N2 for 20 minutes. The resultant mixture was cooled to 0° C. and then treated with methyl iodide (6.16 g, 43.4 mmol) and then warmed to room temperature and stirred for 16 h. The reaction was quenched with aqueous 1 N HCl (60 mL) and then worked up extractively with EtOAc and water. The organic layer was dried (MgSO4) and the solvent removed in vacuo to give crude product that was purified by flash chromatography using 3:1 hexanes:actetone to afford 7.46 g (85%) [1-(4-methoxy-benzyl)-3-methyl-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl ester. MS (ES+) Calc'd for C15H19N2O5 (M+1) 307. Found m/z 307 (100%). 1H NMR.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 16 h
  3. customThe reaction was quenched with aqueous 1 N HCl (60 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give crude product that
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-0746ee4bfe0442f1bb2d7bfb6b0e97c0
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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