[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]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.
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