Sodium hydride → (R)-3-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)-5-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-one

HRID 856353노트

반응식

HRID 856353 반응식
Cl[C:2]1[N:3]([CH2:10][C@:11]([OH:31])([CH3:30])[CH2:12][N:13]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[O:15][C:14]2=[O:29])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+]>O1CCOCC1>[CH3:30][C@@:11]1([CH2:12][N:13]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[O:15][C:14]2=[O:29])[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

4

반응물 2

HCID 24758Sodium hydrideHCID 69481895(R)-3-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-5-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-one

생성물 1

HCID 69480520(R)-3-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)-5-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-one수율 40%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of (R)-3-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-5-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-one prepared in Example 539 (0.87 g, 1.88 mmol) in 1,4-dioxane (18 ml), sodium hydride (98 mg, 2.44 mmol) was added with cooling on ice-bath. The mixture was stirred under reflux for 5 hours, concentrated under reduced pressure, then water was added with cooling on ice-bath. The solution was extracted with ethyl acetate, and the organic phase was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate 9/1), and recrystallized from acetonitrile/isopropanol to afford (R)-3-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)-5-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-one (0.32 g, yield 40%) as a white powder.

후처리

  1. temperaturewith cooling on ice-bath
  2. temperatureunder reflux for 5 hours
  3. concentrationconcentrated under reduced pressure
  4. additionwater was added
  5. temperaturewith cooling on ice-bath
  6. extractionThe solution was extracted with ethyl acetate
  7. dry with materialthe organic phase was dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate 9/1)
  10. customrecrystallized from acetonitrile/isopropanol

출처 및 근거

ORD 기록
ord-31c32727514d46bfbc16ce3a4da705f6
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262212B2

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