Dimethylformamide → 3-(4-Trifluoromethylphenyl)-2-propenyl (S)-4-[3-(2-bromo-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]piperazine-1-carboxylate

HRID 856384노트

반응식

HRID 856384 반응식
[Br:1][C:2]1[N:3]([CH2:10][C@:11]2([CH3:14])[CH2:13][O:12]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[N:15]1([C:21]([O:23][CH2:24][CH:25]=[CH:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.CN(C=O)C>O>[Br:1][C:2]1[N:3]([CH2:10][C@:11]([OH:12])([CH3:14])[CH2:13][N:18]2[CH2:17][CH2:16][N:15]([C:21]([O:23][CH2:24][CH:25]=[CH:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:35])([F:36])[F:34])=[CH:29][CH:28]=3)=[O:22])[CH2:20][CH2:19]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 10467858(R)-2-bromo-4-nitro-1-(2-methyl-2-oxiranylmethyl)imidazoleHCID 665893003-(4-Trifluoromethylphenyl)-2-propenyl piperazine-1-carboxylate

생성물 1

HCID 866043783-(4-Trifluoromethylphenyl)-2-propenyl (S)-4-[3-(2-bromo-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]piperazine-1-carboxylate수율 84.1%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

A mixture of (R)-2-bromo-4-nitro-1-(2-methyl-2-oxiranylmethyl)imidazole (2.04 g, 7.78 mmol), 3-(4-trifluoromethylphenyl)-2-propenyl piperazine-1-carboxylate (2.69 g, 8.56 mmol) and N,N′-dimethylformamide (10 ml) was stirred at 50° C. for 20 hours. The reaction solution was allowed to return to room temperature, water was added, and the resultant solution was extracted with ethyl acetate (15 ml) twice. The organic phases were combined, washed with water three times, and dried over sodium sulfate. After filtration, the filtrate was concentrated, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/2) to obtain 3-(4-trifluoromethylphenyl)-2-propenyl (S)-4-[3-(2-bromo-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]piperazin-1-carboxylate (3.77 g, 84%) as a yellow oil.

후처리

  1. customto return to room temperature
  2. extractionthe resultant solution was extracted with ethyl acetate (15 ml) twice
  3. washwashed with water three times
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/2)

출처 및 근거

ORD 기록
ord-df8658ff6aea4ba8aa41fd8ec99279cb
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262212B2

반응 노트

불러오는 중…