Selenium Dioxide → Ethyl 2-(2-t-pentyloxycarbonylamino-1,3-thiazol-4-yl)glyoxylate

HRID 638414Notes

Reaction equation

HRID 638414 reaction equation
[Se](=O)=[O:2].[C:4]([O:9][C:10]([NH:12][C:13]1[S:14][CH:15]=[C:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:17]=1)=[O:11])([CH2:7][CH3:8])([CH3:6])[CH3:5]>O1CCOCC1.O>[C:4]([O:9][C:10]([NH:12][C:13]1[S:14][CH:15]=[C:16]([C:18](=[O:2])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:17]=1)=[O:11])([CH2:7][CH3:8])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 24007Selenium Dioxide2×HCID 19978738Ethyl 2-(2-t-pentyloxycarbonylamino-1,3-thiazol-4-yl)acetateHCID 178470763HCID 178470763, compound

Product 1

HCID 19978748Ethyl 2-(2-t-pentyloxycarbonylamino-1,3-thiazol-4-yl)glyoxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of selenium dioxide (0.11 g.) in a mixture of dioxane (2.5 ml.) and water (0.1 ml.) was added a mixture of ethyl 2-(2-tert-pentyloxycarbonylamino-1,3-thiazol-4-yl)acetate, which can be represented as ethyl 2-(tert-pentyloxycarbonylimino-2,3-dihydro-1,3-thiazol-4-yl)acetate, (0.3 g.) and dioxane (2.5 ml.) at 110° C. with stirring. The mixture was stirred for 30 minutes at the same temperature, and selenium dioxide (0.055 g.) was further added thereto and then the mixture was stirred for 1.5 hours at the same temperature. After the reaction, the reaction liquid is separated by decantation, and the residue was washed with a small amount of dioxane. The reaction liquid and washing are combined together, and then the solvents were distilled off. The residue was dissolved in ethyl acetate. The solution was washed with water and dried and then the solvent was distilled off to give brown oil of ethyl 2-(2-tert-pentyloxycarbonylamino-1,3-thiazol-4-yl)glyoxylate, which can be represented as ethyl 2-(tert-pentyloxycarbonylimino-2,3-dihydro-1,3-thiazol-4-yl)-glyoxylate, (0.22 g.).

Workup

  1. additionwas added
  2. additionwas further added
  3. stirringthe mixture was stirred for 1.5 hours at the same temperature
  4. customAfter the reaction
  5. customthe reaction liquid
  6. customis separated by decantation
  7. washthe residue was washed with a small amount of dioxane
  8. customThe reaction liquid
  9. washwashing
  10. distillationthe solvents were distilled off
  11. dissolutionThe residue was dissolved in ethyl acetate
  12. washThe solution was washed with water
  13. customdried
  14. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-660df5dc22074f0e946c9c4c0bd81171
Source dataset
uspto-grants-1985_12
Patent number
US04560765

Reaction notes

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