Selenium Dioxide → HCID 86589729, compound

HRID 896265Notes

Reaction equation

HRID 896265 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[S:9][C:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N:7][CH:6]=1.[Se](=O)=[O:20].C(Cl)Cl.CO>O1CCOCC1>[CH3:1][O:2][C:3](=[O:18])[C:4]([C:5]1[S:9][C:8]([NH:10][C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])=[N:7][CH:6]=1)=[O:20]

Participants

5

Reactant 3

HCID 24007Selenium DioxideHCID 21226129Dichloromethane methanolHCID 22349665HCID 22349665, compound

Product 1

HCID 86589729HCID 86589729, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl(2-tert-butoxycarbonylamino 1,3-thiazole-5-yl)acetate (4.08 g, 15 mmol) in dioxane (60 ml) was reacted with selenium dioxide (4 g, 36 mmol) at reflux for 45 minutes. The mixture was cooled, CH2Cl2/MeOH 8/2 (150 ml) was added, the insoluble material was filtered, the organic phase was washed with a saturated solution of sodium bicarbonate, and extracted with CH2Cl2, dried, purified by chromatography over alumina, eluant CH2Cl2/MeOH 9/1 to give title compound (1 g, 23%).

Workup

  1. temperatureat reflux for 45 minutes
  2. temperatureThe mixture was cooled
  3. filtrationthe insoluble material was filtered
  4. washthe organic phase was washed with a saturated solution of sodium bicarbonate
  5. extractionextracted with CH2Cl2
  6. customdried
  7. custompurified by chromatography over alumina, eluant CH2Cl2/MeOH 9/1

Sources & evidence

ORD record
ord-fff1dc9e449243ddaec97c8e179eea7b
Source dataset
uspto-grants-2005_07
Patent number
US06919338B2

Reaction notes

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