1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 10104781, compound

HRID 856159Notes

Reaction equation

HRID 856159 reaction equation
[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

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86604804HCID 86604804, compound

Product 1

HCID 10104781HCID 10104781, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(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.

Workup

  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)

Sources & evidence

ORD record
ord-1b1dec345b224d8e8ffe10f050862707
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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