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Water → O-chloroacetylcarbamoyl fumagillol

HRID 1646631
Notes
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Reaction equation

HRID 1646631 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 218852-DimethylaminopyridineHCID 78209Chloroacetyl isocyanateHCID 222778Fumagillol

Product 1

HCID 14942883O-chloroacetylcarbamoyl fumagillolYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

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

  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)

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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes