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Ethyl Acetate → 5-[3-(2-dimethylamino-ethylamino)-propyl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester

HRID 2191440
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2191440
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:26])=[C:8]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[NH:9][C:10]=1[CH2:11][CH2:12][CH2:13]OS(C)(=O)=O)=[O:5])[CH3:2].[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30][NH2:31].C(OCC)(=O)C>[Cl-].[Na+].O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:26])=[C:8]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[NH:9][C:10]=1[CH2:11][CH2:12][CH2:13][NH:31][CH2:30][CH2:29][N:28]([CH3:32])[CH3:27])=[O:5])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 66053N,N-DimethylethylenediamineHCID 592500502-(tert-butyl) 4-ethyl 3-methyl-5-(3-((methylsulfonyl)oxy)propyl)-1H-pyrrole-2,4-dicarboxylate

Produkt 1

HCID 592500755-[3-(2-dimethylamino-ethylamino)-propyl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl esterAusbeute 59,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360
Sodium chloride; water
Lösungsmittel

Versuchsvorschrift

5-(3-Methanesulfonyloxy-propyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 1 g (11.964 g, 25.7 mmol) obtained from step 6 of Example 1 was dissolved in N,N-dimethylethylenediamine (12 ml, 97 mmol), the resulting solution was stirred for 5 hours at room temperature. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was added with ethyl acetate (80 ml) and saturated brine (80 ml), stirred for 5 minutes, and separated into layers. The organic phase was washed with saturated brine (80 ml×4) to remove N,N-dimethylethylenediamine, dried over anhydrous magnesium sulfate, filtered to remove the drying agent and concentrated under reduced pressure to obtain brown oil. The residue was purified by silica gel column chromatography to obtain the title compound 5-[3-(2-dimethylamino-ethylamino)-propyl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 23a (5.85 g, yield 45.9%) as a yellow oil.

Aufarbeitung

  1. stirringstirred for 5 minutes
  2. customseparated into layers
  3. washThe organic phase was washed with saturated brine (80 ml×4)
  4. customto remove N,N-dimethylethylenediamine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customto remove the drying agent
  8. concentrationconcentrated under reduced pressure
  9. customto obtain brown oil
  10. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cd109e02247847ccb3c6ac09697344a7
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08329682B2

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