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

HRID 856159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 856159
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 10104781HCID 10104781, VerbindungAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-1b1dec345b224d8e8ffe10f050862707
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07262212B2

Notizen zur Reaktion

Wird geladen…