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

HRID 1985183Notes

Reaction equation

HRID 1985183 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH:5]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[C:7](=[O:22])[NH:6]1.[H-].[Na+].[Cl-].CN([CH:30]=[O:31])C>>[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH:5]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[C:7](=[O:22])[N:6]1[CH2:11][C:12]1[CH:21]=[CH:20][C:19]([O:31][CH3:30])=[CH:14][CH:13]=1

Participants

5

Reactant 4

HCID 312ChlorideHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 57719019(1-Naphthalen-2-ylmethyl-2,5-dioxo-imidazolidin-4-yl)-acetic acid methyl ester

Product 1

HCID 57719170[3-(4-Methoxy-benzyl)-1-naphthalen-2-ylmethyl-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl esterYield 95%

Procedure

A 0° C. solution of compound (1-naphthalen-2-ylmethyl-2,5-dioxo-imidazolidin-4-yl)-acetic acid methyl ester (6.29 g, 20.1 mmol) in DMF (60 mL) is treated with sodium hydride (60% dispersion, 0.97 g, 24.3 mmol) and warmed to room temperature and stirred under N2 for 20 minutes. The resultant mixture is cooled to 0° C. and then treated with 4-methoxybenzyl, chloride (6.35 g, 40.6 mmol) and then warmed to room temperature and stirred for 16 hours. The reaction is quenched with aqueous 1 N HCl (100 mL) and then worked up extractively with Et2O and water. The organic layer is dried and the solvent removed to give crude product that is purified by flash chromatography using a gradient of 4:1 hexanes:acetone to afford 8.31 g (95%) [3-(4-methoxy-benzyl)-1-naphthalen-2-ylmethyl-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl ester. Rf=0.44 (1:1 hexanes:acetone). 1H NMR.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 16 hours
  3. customThe reaction is quenched with aqueous 1 N HCl (100 mL)
  4. customThe organic layer is dried
  5. customthe solvent removed
  6. customto give crude product that
  7. customis purified by flash chromatography

Sources & evidence

ORD record
ord-b340af43658d4e4086c4ab1adb7fbd76
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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