Sodium hydride → (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-trifluoromethylphenoxy)piperidine-1-carboxylate

HRID 856207노트

반응식

HRID 856207 반응식
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:32]=[CH:31][C:6]([O:7][CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C@@:18]([OH:30])([CH3:29])[CH2:19][N:20]3[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[N:22]=[C:21]3Cl)=[O:15])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1.[H-].[Na+]>CN(C=O)C>[F:1][C:2]([F:34])([F:33])[C:3]1[CH:32]=[CH:31][C:6]([O:7][CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C@:18]3([CH3:29])[O:30][C:21]4=[N:22][C:23]([N+:25]([O-:27])=[O:26])=[CH:24][N:20]4[CH2:19]3)=[O:15])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1

참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 69481041(R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethylphenoxy)-piperidine-1-carboxylate

생성물 1

HCID 69482992(R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-trifluoromethylphenoxy)piperidine-1-carboxylate수율 47.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To the solution of (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethylphenoxy)piperidine-1-carboxylate prepared in Example 104 (0.18 g, 0.36 mmol) in DMF (2 ml), sodium hydride (19 mg, 0.47 mmol) was added followed by stirring for 1.5 hours with cooling on ice-bath. To the reaction mixture, ice-water was added, and the solution was extracted with ethyl acetate. The organic phase was washed with water, 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 isopropanol to afford (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-trifluoromethylphenoxy)piperidine-1-carboxylate (0.08 g, yield 47%) as a white solid.

후처리

  1. temperaturewith cooling on ice-bath
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1)
  7. customrecrystallized from isopropanol

출처 및 근거

ORD 기록
ord-663684a4030f4d649487c571af0faa2e
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262212B2

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