Metaperiodic acid → HCID 58522465, compound

HRID 718054Notes

Reaction equation

HRID 718054 reaction equation
[CH3:1][S:2][C:3]1[C:13]2[O:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[N:9]=[C:8]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.I(O)(=O)(=O)=[O:29]>C(#N)C.[Fe](Cl)(Cl)Cl>[CH3:1][S:2]([C:3]1[C:13]2[O:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[N:9]=[C:8]([C:18]3[CH:19]=[CH:20][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:26][CH:27]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[O:29]

Participants

5

Reactant 2

HCID 65185Metaperiodic acidHCID 59783844HCID 59783844, compound

Product 1

HCID 58522465HCID 58522465, compoundYield 57.6%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6342AcetonitrileSolvent

Procedure

To a stirring suspension of compound 98 (100 mg, 0.266 mmol) and iron (III) chloride (1.296 mg, 7.99 μmol) in acetonitrile (2 mL) after 5 minutes was added periodic acid (66.8 mg, 0.293 mmol) in one portion. The reaction mixture was left to stir at room temperature overnight then quenched with saturated sodium thiosulfate solution and diluted with ethyl acetate. The organic layer was washed with water, brine, dried over MgSO4, filtered and solvent evaporated. Purification via ISCO (0-40% EtOAc/Hexanes; 40 g silica gel column) afforded title compound 99 (60 mg, 57%) as a yellow solid. LRMS (ESI): (calc) 391.09. (found) 392.4 (MH)+.

Workup

  1. waitThe reaction mixture was left
  2. customthen quenched with saturated sodium thiosulfate solution
  3. additiondiluted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customsolvent evaporated
  8. customPurification via ISCO (0-40% EtOAc/Hexanes; 40 g silica gel column)

Sources & evidence

ORD record
ord-09e981c4c3fb4e7f9d5ce7db31d84408
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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