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

HRID 856206ノート

反応式

HRID 856206 の反応式
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C@@:20]([OH:32])([CH3:31])[CH2:21][N:22]3[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[N:24]=[C:23]3Cl)=[O:17])[CH2:12][CH2:11]2)=[CH:5][CH:4]=1.[H-].[Na+]>CN(C=O)C>[F:1][C:2]([F:34])([F:33])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C@:20]3([CH3:31])[O:32][C:23]4=[N:24][C:25]([N+:27]([O-:29])=[O:28])=[CH:26][N:22]4[CH2:21]3)=[O:17])[CH2:12][CH2:11]2)=[CH:5][CH:4]=1

参加物

4

反応物 2

HCID 24758Sodium hydrideHCID 69479082(R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethylphenylamino)piperidine-1-carboxylate

生成物 1

HCID 69481331(R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-trifluoromethylphenylamino)piperidine-1-carboxylate収率 31.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To the solution of (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethylphenylamino)piperidine-1-carboxylate prepared in Example 105 (1.44 g, 2.85 mmol) in DMF (10 ml), sodium hydride (0.14 g, 3.42 mmol) was added followed by stirring for 1 hour 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 (ethyl acetate) and recrystallized from acetonitrile-isopropanol to afford (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-trifluoromethylphenylamino)piperidine-1-carboxylate (0.42 g, yield 31%) as a white solid.

後処理

  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 (ethyl acetate)
  7. customrecrystallized from acetonitrile-isopropanol

出典と根拠

ORDレコード
ord-d2a584e0e21b4c779f76cd16dcaee767
出典データセット
uspto-grants-2007_08
特許番号
US07262212B2

反応ノート

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