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Water → O-chloroacetylcarbamoyl fumagillol

HRID 846050
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 846050
[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), chloroacetyl isocyanate (160 mg) was added dropwise with ice-cooling, followed by addition of dimethylaminopyridine (130 mg) and stirring at 0° C. for 2 hours. The reaction mixture was treated with water and extracted with dichloromethane. The organic layer was washed with saturated saline and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography. The eluate with n-hexane-ethyl acetate (3:1) was concentrated under reduced pressure, to give 318 mg (yield: 71%) of O-chloroacetylcarbamoyl fumagillol as a colorless powder.

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. concentrationThe eluate with n-hexane-ethyl acetate (3:1) was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-36130a49dd59473bb0506cd20b4aee77
Quelldatensatz
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05135920

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