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

HRID 23562

反応式

HRID 23562 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4c3084a0cf56463b889bd6bdadaadc60
出典データセット
uspto-grants-2005_02
特許番号
US06852744B2

関連ノート

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