Water → HCID 69481645, 화합물

HRID 856270노트

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HRID 856270 반응식
Cl[C:2]1[N:3]([CH2:10][C@@:11]([CH3:32])([OH:31])[CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)[CH2:15][CH2:14]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+].O>CN(C=O)C>[CH3:32][C@@:11]1([CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)[CH2:15][CH2:14]2)[O:31][C:2]2=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]2[CH2:10]1

참가 물질

5

반응물 3

HCID 962WaterHCID 24758Sodium hydrideHCID 69479606HCID 69479606, 화합물

생성물 1

HCID 69481645HCID 69481645, 화합물수율 44%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(S)-1-(2-Chloro-4-nitroimidazol-1-yl)-2-methyl-3-[4-(4-trifluoromethylbenzyloxy)piperidin-1-yl]propan-2-ol prepared in Example 254 (1.36 g, 2.8 mmol) was dissolved in DMF (15 ml). To the solution, sodium hydride (134 mg, 3.36 mmol) was added with cooling on ice-bath followed by stirring at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with a saturated saline solution, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=10/1) and crystallized from methylene chloride-diisopropyl ether to afford (S)-2-methyl-6-nitro-2-[4-(4-trifluoromethylbenzyloxy)piperidin-1-ylmethyl]-2,3-dihydroimidazo[2,1-b]oxazole (431 mg, yield 44%) as a white powder.

후처리

  1. temperaturewith cooling on ice-bath
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with a saturated saline solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=10/1)
  8. customcrystallized from methylene chloride-diisopropyl ether

출처 및 근거

ORD 기록
ord-20e39c9ab74f4ccebdff787136b33f8b
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262212B2

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