Water → O-chloroacetylcarbamoyl fumagillol

HRID 1646631Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-b70cbb2026e44f7a835dbd9ce83cc52d
Source dataset: uspto-grants-1993_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05180735

Reaction notes

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