Water → Ethyl 2-(4-carbamoyl-1-imidazolyl)valerate

HRID 278464

反応式

HRID 278464 の反応式
[H-].[Na+].[NH:3]1[CH:7]=[C:6]([C:8]([NH2:10])=[O:9])[N:5]=[CH:4]1.Br[CH:12]([CH2:18][CH2:19][CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14].O>CN(C=O)C>[C:8]([C:6]1[N:5]=[CH:4][N:3]([CH:12]([CH2:18][CH2:19][CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:7]=1)(=[O:9])[NH2:10]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79071Ethyl 2-bromovalerateHCID 152917Imidazole-4-carboxamide

生成物 1

HCID 22628554Ethyl 2-(4-carbamoyl-1-imidazolyl)valerate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
55 °C

実験手順

NaH (60% in mineral oil, 60 mg) was added to a stirred solution of 4-imidazolecarboxamide (obtained in Preparation 1) (167 mg) in DMF (3.5 ml), and the reaction mixture was stirred for 1.5 hours at 55° C. Ethyl 2-bromovalerate (0.153 ml) was added to this mixture, and the reaction mixture was stirred for 3 hours at 55-60° C. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel (12 g) chromatography eluting with chloroform/methanol (25:1) to give ethyl 2-(4-carbamoyl-1-imidazolyl)valerate (150 mg).

後処理

  1. stirringthe reaction mixture was stirred for 3 hours at 55-60° C
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel (12 g) chromatography
  7. washeluting with chloroform/methanol (25:1)

出典と根拠

ORDレコード
ord-a32610157fa241bfa4ddc7d1c261eb8a
出典データセット
uspto-grants-2002_03
特許番号
US06359145B1

関連ノート

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