1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 10104781、化合物

HRID 856159ノート

反応式

HRID 856159 の反応式
[Cl:1][C:2]1[N:3]([CH2:10][C@@:11]([OH:19])([CH3:18])[CH2:12]OS(C)(=O)=O)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[Cl:1][C:2]1[N:3]([CH2:10][C@@:11]2([CH3:18])[CH2:12][O:19]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

参加物

4

反応物 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86604804HCID 86604804、化合物

生成物 1

HCID 10104781HCID 10104781、化合物収率 91.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(S)-2-Chloro-1-(2-hydroxy-2-methyl-3-methanesulfonyloxypropyl)-4-nitroimidazole prepared in Example 17 (3.02 g, 9.51 mmol) was dissolved in methylene chloride (30 ml). DBU (1.7 ml, 11.41 mmol) was added to the solution, and the resulting mixture was stirred at room temperature for 1.5 hours. The reaction mixture was washed with 3N hydrochloric acid (30 ml) and saturated saline solution (20 ml) in this order, dried over magnesium sulfate and then filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=20/1) to afford (S)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole (1.89 g, yield 91%) as a light yellow solid.

後処理

  1. washThe reaction mixture was washed with 3N hydrochloric acid (30 ml) and saturated saline solution (20 ml) in this order
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=20/1)

出典と根拠

ORDレコード
ord-1b1dec345b224d8e8ffe10f050862707
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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