Sodium Iodide → HCID 21256675, compound

HRID 635989Notes

Reaction equation

HRID 635989 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]3[S:14](=O)(=O)[CH2:15][CH2:16][C:12]=3[N:11](C(OC(C)(C)C)=O)[C:10]3[CH2:26][O:27][CH2:28][C:29](=[O:30])[C:9]2=3)=[CH:4][C:3]=1[Sn](C)(C)C.ClN1C(=O)CCC1=O.[I-:43].[Na+].O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(=O)C.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]3[S:14][CH2:15][CH2:16][C:12]=3[NH:11][C:10]3[CH2:26][O:27][CH2:28][C:29](=[O:30])[C:9]2=3)=[CH:4][C:3]=1[I:43]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 31398ChlorosuccinimideHCID 61475Sodium Thiosulfate PentahydrateHCID 18000994HCID 18000994, compound

Product 1

HCID 21256675HCID 21256675, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of the product from Example 37B (0.023 g, 0.038 mmol) in 1% acetic acid in methanol (25 mL) was treated with N-chlorosuccinimide (0.010 g, 0.077 mmol), then treated with sodium iodide (0.011 g, 0.077 mmol), stirred for 10 minutes, treated with pulverized sodium thiosulfate pentahydrate (0.020 g, 0.080 mmol), stirred for 10 minutes and concentrated to dryness. The residue was treated with trifluoroacetic acid (3 mL), stirred at ambient temperature for 15 minutes and concentrated to dryness. The residue was treated with trifluoroacetic acid (3 mL), heated gently on a steam bath for 1 minute, cooled to ambient temperature and concentrated to dryness. The residue was purified by chromatography on silica gel (2% methanol and then 5% methanol in methylene chloride) to provide the title compound (0.0156 g).

Workup

  1. stirringstirred for 10 minutes
  2. concentrationconcentrated to dryness
  3. additionThe residue was treated with trifluoroacetic acid (3 mL)
  4. stirringstirred at ambient temperature for 15 minutes
  5. concentrationconcentrated to dryness
  6. additionThe residue was treated with trifluoroacetic acid (3 mL)
  7. temperatureheated gently on a steam bath for 1 minute
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by chromatography on silica gel (2% methanol

Sources & evidence

ORD record
ord-09ae0197ec1449baa3bce60e7b4f9c5f
Source dataset
uspto-grants-2001_02
Patent number
US06191140B1

Reaction notes

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