Sodium Iodide → HCID 9825532, compound

HRID 478278Notes

Reaction equation

HRID 478278 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]3[S:14](=[O:18])(=[O:17])[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](=[O:18])(=[O:17])[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 9825532HCID 9825532, compoundYield 89%

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-1da90027f6da401cb8f31a043321c56d
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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