Water → HCID 19348409, compound

HRID 1637244Notes

Reaction equation

HRID 1637244 reaction equation
[CH3:1][C:2]([CH3:18])=[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])[CH2:10]1)[CH3:8].[CH3:19][S-:20].O>CN(C=O)C>[O:7]1[CH:5]([CH2:4][CH:3]=[C:2]([CH3:18])[CH3:1])[C:6]1([CH:9]1[CH2:10][CH:11]([OH:17])[CH2:12][CH2:13][C:14]1([CH2:15][S:20][CH3:19])[OH:16])[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 519392MercaptomethanideHCID 46192947HCID 46192947, compound

Product 1

HCID 19348409HCID 19348409, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-demethoxyfumagillol (280 mg) in N,N'-dimethylformamide (2 ml), thiomethoxide (220 mg) was added, and the mixture was stirred at room temperature for 1 hour. After adding water (20 ml) thereto, the reaction mixture was extracted with isopropyl ether (50 ml). The organic layer was washed with saturated sodium hydrogen carbonate solution (10 ml) and brine (20 ml), dried over anhydrous magnesium sulfate, and filtered. The residue after distilling off the solvent under reduced pressure was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2) to obtain 180 mg of the title compound as white solid.

Workup

  1. extractionthe reaction mixture was extracted with isopropyl ether (50 ml)
  2. washThe organic layer was washed with saturated sodium hydrogen carbonate solution (10 ml) and brine (20 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationThe residue after distilling off the solvent under reduced pressure
  6. customwas purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2)

Sources & evidence

ORD record
ord-fde51cfd54774c1baa1de985e20066cc
Source dataset
uspto-grants-2000_03
Patent number
US06040337

Reaction notes

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