Reaction #1696439

Reaction equation

thiomarinol

OXONE

sodium hydrogencarbonate

→

thiomarinol B

Yield 75.0%

Solvents

water

acetone

water

Conditions

Workup

1. 1
   Temperaturecooled
2. 2
   workup.ADDITION) were added to the resulting solution
3. 3
   Temperaturecooling, for 40 minutes
4. 4
   workup.STIRRINGthe mixture was again stirred, whilst ice-
5. 5
   Temperaturecooling, for 30 minutes
6. 6
   Extractionwas then extracted with a 10:1 by volume mixture of methylene chloride and tetrahydrofuran
7. 7
   DryingThe extract was dried over anhydrous sodium sulfate
8. 8
   Otherthe solvent was removed by distillation under reduced pressure
9. 9
   OtherThe resulting residue was then isolated
10. 10
    Otherpurified by reverse phase, high performance liquid chromatography (

Procedure

100.9 mg of thiomarinol (prepared as described in Example 6) were dissolved in a mixture of 5 ml of acetone and 5 ml of water, and then the resulting solution was ice-cooled. 112.2 mg of OXONE (a trade name for a product of Aldrich Chemical Co., Inc.) were added to the resulting solution, and then the mixture was stirred, whilst ice-cooling, for 40 minutes. At the end of this time, 1.2 ml of a saturated aqueous solution of sodium hydrogencarbonate were added to this mixture, and the mixture was again stirred, whilst ice-cooling, for 30 minutes. 5 ml of water were then added to the reaction mixture, which was then extracted with a 10:1 by volume mixture of methylene chloride and tetrahydrofuran. The extract was dried over anhydrous sodium sulfate, and then the solvent was removed by distillation under reduced pressure. The resulting residue was then isolated and purified by reverse phase, high performance liquid chromatography (using a Senshu Pak ODS-5251-N column, and 40% v/v aqueous acetonitrile as the eluent), to obtain 79.5 mg (yield 75%) of thiomarinol B having a light yellow color and having the physico-chemical properties listed above.

Source