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

HRID 2227471

반응식

HRID 2227471 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-19e89b8f35bd47a78da4095de7164f59
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06414005B1

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