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Water → O-chloroacetylcarbamoyl fumagillol

HRID 1646631
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1646631
[CH3:1][C:2]([CH3:20])=[CH:3][CH2:4][C@H:5]1[O:7][C@@:6]1([C@@H:9]1[C@:14]2([O:16][CH2:15]2)[CH2:13][CH2:12][C@@H:11]([OH:17])[C@H:10]1[O:18][CH3:19])[CH3:8].[Cl:21][CH2:22][C:23]([N:25]=[C:26]=[O:27])=[O:24].CN(C1C=CC=CN=1)C.O>ClCCl>[CH3:1][C:2]([CH3:20])=[CH:3][CH2:4][C@@H:5]1[O:7][C@:6]1([C@@H:9]1[C@:14]2([O:16][CH2:15]2)[CH2:13][CH2:12][C@@H:11]([O:17][C:26]([NH:25][C:23]([CH2:22][Cl:21])=[O:24])=[O:27])[C@H:10]1[O:18][CH3:19])[CH3:8]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 218852-DimethylaminopyridineHCID 78209Chloroacetyl isocyanateHCID 222778Fumagillol

Produkt 1

HCID 14942883O-chloroacetylcarbamoyl fumagillolAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of fumagillol (314 mg) in dichloromethane (5 ml) was added dropwise, under cooling with ice, chloroacetylisocyanate (160 mg), to which was then added dimethylaminopyridine (130 mg), followed by stirring at 0° C. for two hours. To the reaction mixture was added water, which was subjected to extraction with dichloromethane. The organic layer was washed with a saturated aqueous saline solution, then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by means of a silica gel column chromatography (carrier 20 g, developing solvent: ethylacetate-hexane=1:2) to afford O-chloroacetylcarbamoyl fumagillol (318 mg: yield 71%) as colorless powder.

Aufarbeitung

  1. extractionwas subjected to extraction with dichloromethane
  2. washThe organic layer was washed with a saturated aqueous saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by means of a silica gel column chromatography (carrier 20 g, developing solvent: ethylacetate-hexane=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-b70cbb2026e44f7a835dbd9ce83cc52d
Quelldatensatz
uspto-grants-1993_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05180735

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