Water → Phenylmethyl 2-(2,5-dioxo-3-benzylimidazolidinyl)acetate

HRID 23562

Reaction equation

HRID 23562 reaction equation
[O:1]=[C:2]1[NH:6][CH2:5][C:4](=[O:7])[N:3]1[CH2:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].CC(C)([O-])C.[Li+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>CN(C=O)C>[O:1]=[C:2]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:5][C:4](=[O:7])[N:3]1[CH2:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 22574607Phenylmethyl 2-(2,5-dioxoimidazolidinyl)acetateHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)

Product 1

HCID 22574604Phenylmethyl 2-(2,5-dioxo-3-benzylimidazolidinyl)acetateYield 62.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of phenylmethyl 2-(2,5-dioxoimidazolidinyl)acetate (4.0 g, 16.1 mmol) in DMF (50 ml) at 0° C. were added lithium tert-butoxide (1.6 g, 19.3 mmol) and benzyl bromide (2.1 ml, 17.7 mmol). After stirring the mixture at room temperature overnight, the reaction mixture was poured into water (100 ml) and the mixture was extracted with ethyl acetate. The organic phase was washed with water, 10% aqueous citric acid solution, saturated aqueous sodium hydrogen carbonate solution and brine. The organic solution was dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel, n-hexane:ethyl acetate=3:1) to give phenylmethyl 2-(2,5-dioxo-3-benzylimidazolidinyl)acetate (3.42 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with water, 10% aqueous citric acid solution, saturated aqueous sodium hydrogen carbonate solution and brine
  3. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel, n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-4c3084a0cf56463b889bd6bdadaadc60
Source dataset
uspto-grants-2005_02
Patent number
US06852744B2

Linked notes

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