Selenium Dioxide → HCID 53744588, compound

HRID 905411Notes

Reaction equation

HRID 905411 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[N:10]=[C:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[S:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Se](=O)=[O:21]>O1CCOCC1.O>[C:1]([O:5][C:6]([NH:8][C:9]1[N:10]=[C:11]([C:14](=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[S:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 19790263HCID 19790263, compound

Product 1

HCID 53744588HCID 53744588, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Ethyl 2-(4-tert-butoxycarbonylaminothiazol-2-yl)acetate (5.1 g) was added to a solution of selenium dioxide (2.96 g) in dioxane (60 ml) and water (2 ml) at 110° C. and stirred for 4.5 hours at 110° C. The mixture was evaporated and the residue was dissolved in ethyl acetate and water. The separated ethyl acetate layer was washed with an aqueous sodium chloride and dried over magnesium sulfate. After removing the solvent, the residue was subjected to column chromatography on silica gel and eluted with methylene chloride. The fraction containing an object compound was evaporated to give ethyl (4-tert-butoxycarbonylaminothiazol-2-yl)glyoxylate (4.2 g).

Workup

  1. customThe mixture was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe separated ethyl acetate layer was washed with an aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customAfter removing the solvent
  6. washeluted with methylene chloride
  7. additionThe fraction containing an object compound
  8. customwas evaporated

Sources & evidence

ORD record
ord-c06894c447ba4bbcbe1f3e126bbc9d6d
Source dataset
uspto-grants-1983_12
Patent number
US04423213

Reaction notes

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