Ethyl nitroacetate → 3-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-2-nitro-propionic Acid Ethyl Ester

HRID 11697

Reaktionsgleichung

Reaktionsgleichung von HRID 11697
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][N+:6]([O-:8])=[O:7])[CH3:2].C(=O)(O)[O-].[Na+].[Cl:15][C:16]1[CH:41]=[CH:40][C:19]([O:20][CH2:21][C:22]([N:24]2[CH2:29][C@H:28]([CH3:30])[N:27]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[CH2:26][C@H:25]2[CH3:39])=[O:23])=[C:18]([CH2:42]Cl)[CH:17]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH2:1]([O:3][C:4](=[O:9])[CH:5]([N+:6]([O-:8])=[O:7])[CH2:42][C:18]1[CH:17]=[C:16]([Cl:15])[CH:41]=[CH:40][C:19]=1[O:20][CH2:21][C:22]([N:24]1[CH2:29][C@H:28]([CH3:30])[N:27]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=2)[CH2:26][C@H:25]1[CH3:39])=[O:23])[CH3:2]

Komponenten

6

Edukt 3

HCID 69379Ethyl nitroacetateHCID 516892Sodium BicarbonateHCID 234058422-[4-Chloro-2-(chloromethyl)phenoxy]-1-{(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl}ethan-1-one

Produkt 1

HCID 865911673-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-2-nitro-propionic Acid Ethyl EsterAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To nitro-acetic acid ethyl ester (0.32 g, 2.39 mmol), sodium bicarbonate (0.10 g, 1.19 mmol) and tetrabutyl ammonium iodide (0.088 g, 0.24 mmol) in dimethyl formamide (5 ml) was added 2-(4-chloro-2-chloromethyl-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.52 g, 1.19 mmol). After 1 hour of heating at 60° C. the reaction was concentrated and then diluted with methylene chloride. After washing with aqueous saturated sodium bicarbonate and saturated sodium chloride the organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (0.30 g).

Aufarbeitung

  1. concentrationwas concentrated
  2. additiondiluted with methylene chloride
  3. washAfter washing with aqueous saturated sodium bicarbonate and saturated sodium chloride the organic layer
  4. dry with materialwas dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-34e48198b45f4c59b72297ec362acb71
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098212B2

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