Water → 3-(4-trifluoromethylphenyl)-2-propenyl (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate

HRID 856385노트

반응식

HRID 856385 반응식
Br[C:2]1[N:3]([CH2:10][C@:11]([OH:36])([CH3:35])[CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][CH:23]=[CH:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[O:20])[CH2:15][CH2:14]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+].C(OCC)(=O)C.O>CN(C=O)C>[CH3:35][C@@:11]1([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][CH:23]=[CH:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[O:20])[CH2:15][CH2:14]2)[O:36][C:2]2=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]2[CH2:10]1

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 866043783-(4-Trifluoromethylphenyl)-2-propenyl (S)-4-[3-(2-bromo-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]piperazine-1-carboxylate

생성물 1

HCID 866043773-(4-trifluoromethylphenyl)-2-propenyl (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate수율 69%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3-(4-Trifluoromethylphenyl)-2-propenyl (S)-4-[3-(2-bromo-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]piperazine-1-carboxylate (3.5 g, 6.07 mmol) was dissolved in N,N′-dimethylformamide (10.5 ml), and sodium hydride (316 mg, 7.89 mmol) was added while cooling on ice followed by stirring at the same temperature for 1.5 hours. To the reaction solution, ethyl acetate (3.5 ml) and water (24.5 ml) were added followed by stirring for 30 minutes. The precipitated crystals were filtered off, washed with water, and purified by silica gel column chromatography (ethyl acetate). Recrystallization from 2-propanol/water gives a light yellow powder of 3-(4-trifluoromethylphenyl)-2-propenyl (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate (2.07 g, 69%).

후처리

  1. temperaturewhile cooling on ice
  2. stirringby stirring for 30 minutes
  3. filtrationThe precipitated crystals were filtered off
  4. washwashed with water
  5. custompurified by silica gel column chromatography (ethyl acetate)
  6. customRecrystallization from 2-propanol/water

출처 및 근거

ORD 기록
ord-64577b126b8540f690cb50631d34f84c
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262212B2

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