Dimethylformamide → HCID 69635160, Verbindung

HRID 856297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 856297
[Cl:1][C:2]1[N:3]([CH2:10][C@@:11]2([CH3:14])[CH2:13][O:12]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[N:15]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.CN(C=O)C>O>[Cl:1][C:2]1[N:3]([CH2:10][C@@:11]([OH:12])([CH3:14])[CH2:13][N:18]2[CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 10104781HCID 10104781, Verbindung

Produkt 1

HCID 69635160HCID 69635160, VerbindungAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
57.5 °C

Versuchsvorschrift

A mixture of (S)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole prepared in Example 18 (440 mg, 2.02 mmol), tert-butyl piperazine-1-carboxylate (414 mg, 2.22 mmol) and DMF (4 ml) was stirred at 55-60° C. for 9 hours. The reaction mixture was allowed to return to room temperature, then diluted with water (24 ml), and the solution was extracted with ethyl acetate (10 ml) twice. The organic phases were combined, washed with water (20 ml) three times and a saturated saline solution (10 ml), dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue treated with diethyl ether to afford tert-butyl (R)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]piperazine-1-carboxylate (662 mg, yield 81%) as a light yellow powder.

Aufarbeitung

  1. customto return to room temperature
  2. extractionthe solution was extracted with ethyl acetate (10 ml) twice
  3. washwashed with water (20 ml) three times
  4. dry with materiala saturated saline solution (10 ml), dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. additionthe residue treated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e030abad630347468b93ef58ff355e25
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07262212B2

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