Sodium Bicarbonate → HCID 9810000, compound

HRID 1609257Notes

Reaction equation

HRID 1609257 reaction equation
[CH3:1][CH:2]([CH:41]([OH:43])[CH3:42])/[CH:3]=[CH:4]/[CH2:5][CH:6]1[CH:11]([OH:12])[CH:10]([OH:13])[CH:9]([CH:14]([OH:40])/[C:15](/[CH3:39])=[CH:16]/[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([NH:29][C:30]2[C:37](=[O:38])[NH:36][C:32]3=[CH:33]S[S:35][C:31]=23)=[O:28])=[O:18])[O:8][CH2:7]1.O[O:45][S:46]([O-:48])=O.[K+].C(=O)([O-])O.[Na+]>CC(C)=O.O>[CH3:1][C@@H:2]([C@@H:41]([OH:43])[CH3:42])/[CH:3]=[CH:4]/[CH2:5][C@@H:6]1[C@@H:11]([OH:12])[C@@H:10]([OH:13])[C@H:9]([C@H:14]([OH:40])/[C:15](/[CH3:39])=[CH:16]/[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([NH:29][C:30]2[C:37](=[O:38])[NH:36][C:32]3=[CH:33][S:46]([S:35][C:31]=23)(=[O:48])=[O:45])=[O:28])=[O:18])[O:8][CH2:7]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 5825095thiomarinolHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 9810000HCID 9810000, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

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.

Workup

  1. temperaturecooled
  2. addition) were added to the resulting solution
  3. temperaturecooling, for 40 minutes
  4. stirringthe mixture was again stirred, whilst ice-
  5. temperaturecooling, for 30 minutes
  6. extractionwas then extracted with a 10:1 by volume mixture of methylene chloride and tetrahydrofuran
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. customthe solvent was removed by distillation under reduced pressure
  9. customThe resulting residue was then isolated
  10. custompurified by reverse phase, high performance liquid chromatography (

Sources & evidence

ORD record
ord-dc1bee2d39a046baa43c7318e2c9f02b
Source dataset
uspto-grants-1995_03
Patent number
US05399711

Reaction notes

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