Ethyl Acetate → HCID 18670554, compound

HRID 1059412Notes

Reaction equation

HRID 1059412 reaction equation
C([C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3[N:12]=[CH:13][CH:14]=[N:15][C:9]=3[N:8]([CH2:16][O:17][CH3:18])[C:7]=2[CH:19]=1)=C.C[N+]1([O-])CC[O:24]CC1.C([O:31][CH2:32][CH3:33])(=O)C>CC(C)=O.C(O)(C)(C)C.[Os](=O)(=O)(=O)=O>[CH3:18][O:17][CH2:16][N:8]1[C:7]2[CH:19]=[C:3]([CH:32]([OH:31])[CH2:33][OH:24])[CH:4]=[CH:5][C:6]=2[S:11][C:10]2[N:12]=[CH:13][CH:14]=[N:15][C:9]1=2

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 18670397HCID 18670397, compound

Product 1

HCID 18670554HCID 18670554, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 6386tert-ButanolSolvent

Procedure

To 30 ml of a solution of 2.6 g of 8-vinyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine and 1.06 g of N-methylmorpholine oxide in acetone was added 4.2 ml of a 1% solution of osmium tetraoxide in tert-butanol and the resulting mixture was stirred at room temperature for 12 hours. Then it was distributed into an aqueous solution of sodium hydrogenthiosulfate and ethyl acetate. After filtering off the inorganic matters through celite, the organic layer was extracted, washed with water and dried over anhydrous sodium sulfate and the extract was filtered. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 0.35 g of the title compound as yellow crystals.

Workup

  1. filtrationAfter filtering off the inorganic matters through celite
  2. extractionthe organic layer was extracted
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationthe extract was filtered
  6. distillationAfter distilling off the solvent under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-93946332709b49378ddaca80e5f5091d
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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