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Sodium hydride → tert-butyl(R)-4-[2-chloro-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethoxy)phenyl]piperazine-1-carboxylate

HRID 856224
ノート
印刷プレビュー

反応式

HRID 856224 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1.[H-].[Na+].Cl[C:25]1[N:26]([CH2:33][C@:34]2([CH3:37])[CH2:36][O:35]2)[CH:27]=[C:28]([N+:30]([O-:32])=[O:31])[N:29]=1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:36][C@:34]2([CH3:37])[O:35][C:25]3=[N:29][C:28]([N+:30]([O-:32])=[O:31])=[CH:27][N:26]3[CH2:33]2)[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 10443353(R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazoleHCID 23081264Tert-butyl 4-(2-chloro-4-hydroxyphenyl)-piperazine-1-carboxylate

生成物 1

HCID 69635433tert-butyl(R)-4-[2-chloro-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethoxy)phenyl]piperazine-1-carboxylate収率 55%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
80 °C

実験手順

Tert-butyl 4-(2-chloro-4-hydroxyphenyl)-piperazine-1-carboxylate (2.7 g, 8.63 mmol) was dissolved in DMF (20 ml). To the solution, sodium hydride (397 mg, 9.92 mmol) was added at room temperature, and the solution was stirred for 20 minutes at 80° C. To the solution, (R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole prepared in Example 12 (2.1 g, 9.50 mmol) was added with cooling on ice-bath, and the solution was stirred for further 20 minutes at 80° C. To the reaction mixture, ice-water was added, and the solution was stirred vigorously. The precipitates were filtered off, washed with water and dissolved in methylene chloride. The solution was washed with a saturated saline solution, dried over magnesium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=200/1) and then crystallized from methylene chloride-ethyl acetate to afford tert-butyl (R)-4-[2-chloro-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethoxy)phenyl]piperazine-1-carboxylate (2.34 g, yield 55%) as a white powder.

後処理

  1. temperaturewith cooling on ice-bath
  2. stirringthe solution was stirred for further 20 minutes at 80° C
  3. stirringthe solution was stirred vigorously
  4. filtrationThe precipitates were filtered off
  5. washwashed with water
  6. dissolutiondissolved in methylene chloride
  7. washThe solution was washed with a saturated saline solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe resulting filtrate was concentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=200/1)
  12. customcrystallized from methylene chloride-ethyl acetate

出典と根拠

ORDレコード
ord-1b154bcb70c842d6a296b6284e1c4b0c
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07262212B2

反応ノート

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