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

HRID 648396Notes

Reaction equation

HRID 648396 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

5

Reactant 2

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

Product 1

HCID 19978748Ethyl 2-(2-t-pentyloxycarbonylamino-1,3-thiazol-4-yl)glyoxylateYield 70.6%

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 (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 were 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 (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-87117b808ec841a98a960a5d2c052f51
Source dataset
uspto-grants-1983_10
Patent number
US04411898

Reaction notes

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