Sodium hydride → N-(5-nitro-2-(pyrrol-1-yl)phenylmethyl)iminodicarboxylic acid di-tert-butyl ester

HRID 2227471ノート

反応式

HRID 2227471 の反応式
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:9])([CH3:6])([CH3:5])[CH3:4].[N+:18]([C:21]1[CH:22]=[CH:23][C:24]([N:29]2[CH:33]=[CH:32][CH:31]=[CH:30]2)=[C:25]([CH:28]=1)[CH2:26]Br)([O-:20])=[O:19]>CN(C)C=O>[C:14]([O:13][C:11]([N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[CH2:26][C:25]1[CH:28]=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=[CH:23][C:24]=1[N:29]1[CH:33]=[CH:32][CH:31]=[CH:30]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 279800Di-tert-butyl IminodicarboxylateHCID 184740025-Nitro-2-(pyrrol-1-yl)benzyl bromide

生成物 1

HCID 54574337N-(5-nitro-2-(pyrrol-1-yl)phenylmethyl)iminodicarboxylic acid di-tert-butyl ester収率 74%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a mixture of sodium hydride (60% content, 21 mg), iminodicarboxylic acid di-tert-butyl ester (117 mg) and dimethylformamide (5 ml), a solution in dimethylformamide (3 ml) of the compound (137 mg) obtained in Example 1c was added dropwise under cooling with ice. The reaction mixture was stirred for 2 hours at room temperature and then concentrated at reduced pressure. Brine was added to the resulting residue and the mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate and then concentrated at reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:9) to give the titled compound (yield, 74%).

後処理

  1. temperatureunder cooling with ice
  2. concentrationconcentrated at reduced pressure
  3. additionBrine was added to the resulting residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. concentrationconcentrated at reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:9)

出典と根拠

ORDレコード
ord-19e89b8f35bd47a78da4095de7164f59
出典データセット
uspto-grants-2002_07
特許番号
US06414005B1

反応ノート

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