Water → HCID 19801008, compound

HRID 1646637Notes

Reaction equation

HRID 1646637 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].[CH3:21][S-:22].O>CN(C=O)C>[O:7]1[CH:5]([CH2:4][CH:3]=[C:2]([CH3:20])[CH3:1])[C:6]1([CH:9]1[CH:10]([O:18][CH3:19])[CH:11]([OH:17])[CH2:12][CH2:13][C:14]1([CH2:15][S:22][CH3:21])[OH:16])[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 222778FumagillolHCID 519392Mercaptomethanide

Product 1

HCID 19801008HCID 19801008, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Fumagillol (3.00 g) was dissolved in DMF (6 ml), to which was added thiomethoxide (2.23 g). The mixture was stirred for 30 minutes, to which was added water to suspend the reaction. The product was extracted with isopropylether. The extract solution was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous saline solution, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, then the residue was purified by means of a silica gel column chromatography (carrier 150 g, developing solvent : ethyl acetate - hexane=1:2), followed by recrystallization from hexane to afford 2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-methylthiomethyl-1,4-cyclohexanediol (2.43 g:yield 69%) as colorless powder, m.p. 52° to 53° C.

Workup

  1. customthe reaction
  2. extractionThe product was extracted with isopropylether
  3. washThe extract solution was washed with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by means of a silica gel column chromatography (carrier 150 g, developing solvent : ethyl acetate - hexane=1:2)
  7. customfollowed by recrystallization from hexane

Sources & evidence

ORD record
ord-af829f4588b1481ea106b05aaffa27f7
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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