Selenium Dioxide → HCID 68130913, compound

HRID 1657706Notes

Reaction equation

HRID 1657706 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C:10]1([O:28][CH3:29])[C:26](=[O:27])[N:12]2[CH:13]([C:18]([O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])=[O:19])[C:14]([CH3:17])=[CH:15][S:16][C@H:11]12)=[O:8].[Se](=O)=O>C(O)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C:10]1([O:28][CH3:29])[C:26](=[O:27])[N:12]2[CH:13]([C:18]([O:20][CH2:21][C:22]([Cl:24])([Cl:25])[Cl:23])=[O:19])[C:14]([CH2:17][O:20][C:18](=[O:19])[CH3:13])=[CH:15][S:16][C@H:11]12)=[O:8]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 68130773HCID 68130773, compound

Product 1

HCID 68130913HCID 68130913, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of β,β,β-trichloroethyl 7-(2-thienylacetamido)-7-methoxy-3-methyl-2-cephem-4-carboxylate 0.94 (mg., 2 mmole) in acetic acid (10 ml.) is added selenium dioxide (0.111 g., 1 mmole) keeping the reaction temperature at about 25°C. The reaction mixture is stirred for two hours, filtered, diluted with water (30 ml.) and extracted with chloroform. The chloroform extracts are washed successively with water, sodium bicarbonate and water. The solvent is removed under vacuum to afford a residue which is chromatographed on silica gel using chloroform and ethyl acetate (95:5) to afford substantially pure β,β,β-trichloroethyl 7-(2-thienylacetamido)-7-methoxy-3-acetoxymethyl-2-cephem-4-carboxylate.

Workup

  1. customat about 25°C
  2. filtrationfiltered
  3. additiondiluted with water (30 ml.)
  4. extractionextracted with chloroform
  5. washThe chloroform extracts are washed successively with water, sodium bicarbonate and water
  6. customThe solvent is removed under vacuum
  7. customto afford a residue which
  8. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-e9a45445c55041c690cb3f321e466cb3
Source dataset
uspto-grants-1976_06
Patent number
US03962231

Reaction notes

Loading…