Sodium hydride → [1-(3,4-Dimethyl-benzyl)-3-(4-methoxy-benzyl)-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl ester

HRID 1985234Notes

Reaction equation

HRID 1985234 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]([CH3:18])=[C:14]([CH3:19])[CH:13]=2)[C:7](=[O:20])[NH:6]1.[H-].[Na+].[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Cl)=[CH:28][CH:27]=1>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]([CH3:18])=[C:14]([CH3:19])[CH:13]=2)[C:7](=[O:20])[N:6]1[CH2:30][C:29]1[CH:32]=[CH:33][C:26]([O:25][CH3:24])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 57719185[1-(3,4-Dimethyl-benzyl)-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl ester

Product 1

HCID 57719133[1-(3,4-Dimethyl-benzyl)-3-(4-methoxy-benzyl)-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl esterYield 102.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 0° C. solution of compound [1-(3,4-dimethyl-benzyl)-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl ester (2.24 g, 7.71 mmol) in DMF (30 mL) was treated with sodium hydride (60% dispersion, 0.37 g, 9.25 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 4-methoxybenzyl chloride (2.41 g, 15.4 mmol) and then warmed to room temperature and stirred for 16 h. The reaction was quenched with 25 mL of aqueous 1 N HCl and then worked up extractively with Et2O 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 a gradient of 5:1 hexanes:actetone to afford 3.23 g (100%) [1-(3,4-dimethyl-benzyl)-3-(4-methoxy-benzyl)-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl ester. MS (ES+) Calc'd for C23H26N2O5 (M+1) 411. Found m/z. 411 (100%). 1H NMR.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 16 h
  3. customThe reaction was quenched with 25 mL of aqueous 1 N HCl
  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-bd61bc77560243f094f6508b2c269041
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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