Sodium Bicarbonate → tert-butyl (S)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-piperazine-1-carboxylate

HRID 856296ノート

反応式

HRID 856296 の反応式
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[CH3:10][C@:11]1([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH2:13][O:12]1.C(=O)([O-])O.[Na+]>C(O)C>[Cl:1][C:2]1[N:3]([CH2:13][C@:11]([OH:12])([CH3:10])[CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 86604816tert-butyl(S)-4-(2-methyloxiran-2-ylmethyl)piperazine-1-carboxylateHCID 178526855HCID 178526855、化合物

生成物 1

HCID 69635130tert-butyl (S)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-piperazine-1-carboxylate収率 45%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To the solution of 2-Chloro-4-nitro-1H-imidazole (89.4 g, 606 mmol) and tert-butyl (S)-4-(2-methyloxiran-2-ylmethyl)piperazine-1-carboxylate (119 g, 466 mmol) in ethanol (475 ml), sodium hydrogen-carbonate (58.7 g, 699 mmol) was added followed by stirring under reflux for 6 hours. The reaction mixture was concentrated under reduced pressure, and the residue was added water. The mixture was extracted with ethyl acetate, and the extract was dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was dispersed into ethyl acetate, and filtered off to afford a solid. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (n-hexane/acetone=3/1) to afford a solid. The solids were combined and dried under reduced pressure to afford tert-butyl (S)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-piperazine-1-carboxylate (84.7 g, yield 45%) as a white powder.

後処理

  1. temperatureunder reflux for 6 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was added water
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe extract was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. additionThe residue was dispersed into ethyl acetate
  9. filtrationfiltered off
  10. customto afford a solid
  11. concentrationThe filtrate was concentrated
  12. customthe residue was purified by silica gel column chromatography (n-hexane/acetone=3/1)
  13. customto afford a solid
  14. customdried under reduced pressure

出典と根拠

ORDレコード
ord-122e7acde26d4de6a8a89cd1d4a04781
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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