Dimethylformamide → 1-[(1R,2R)-1-Methyl-2-hydroxy-2-(2-fluorophenyl)-3-(1H-1,2,4-triazole-1-yl)propyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-4-imidazoline-2-one

HRID 482056

반응식

HRID 482056 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@:8]1([CH2:12][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[C@H:10]([CH3:11])[O:9]1.[F:18][C:19]([F:36])([O:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH:34]=[CH:33][NH:32][C:31]2=[O:35])=[CH:26][CH:25]=1)[CH:20]([F:22])[F:21].[H-].[Na+].CN(C)C=O>O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@:8]([OH:9])([CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1)[C@H:10]([N:32]1[CH:33]=[CH:34][N:30]([C:27]2[CH:26]=[CH:25][C:24]([O:23][C:19]([F:36])([F:18])[CH:20]([F:22])[F:21])=[CH:29][CH:28]=2)[C:31]1=[O:35])[CH3:11]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 104439761-(((2R,3S)-2-(2-fluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazoleHCID 105643671-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone

생성물 1

HCID 30036221-[(1R,2R)-1-Methyl-2-hydroxy-2-(2-fluorophenyl)-3-(1H-1,2,4-triazole-1-yl)propyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-4-imidazoline-2-one수율 8.2%

시약·촉매·용매 1

HCID 962Water용매

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온도
80 °C

실험 절차

(2R,3S)-2-(2-Fluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-yl)methyloxirane (1.5 g), 2.66 g of 1-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone and 0.386 g of 60% sodium hydride in oil were added to 25 ml of N,N-dimethylformamide. The mixture was stirred at 80° C. for 20 hours. After cooling, the reaction mixture was added to 100 ml of water and extracted with ethyl acetate (50 ml×2). The extract was washed with water, dried over anhydrous magnesium sulfate and then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3/2) to give 0.27 g of 1-[(1R,2R)-2-(2-fluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone as a colorless powder.

후처리

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (50 ml×2)
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3/2)

출처 및 근거

ORD 기록
ord-644eff5c728247f98357951c65d507d9
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05792780

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