Sodium Iodide → HCID 22103664, compound

HRID 1457222Notes

Reaction equation

HRID 1457222 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([N:8](COCCOC)[S:9]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[O:25][CH:26]=[CH:27][N:28]=4)=[CH:20][C:19]=3[CH2:29][N:30]3[C:34](=[O:35])[C:33]([CH3:37])([CH3:36])[CH2:32][O:31]3)=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])[O:4][N:3]=1.Cl[Si](C)(C)C.[I-].[Na+]>C(#N)C.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][S:9]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[O:25][CH:26]=[CH:27][N:28]=4)=[CH:20][C:19]=3[CH2:29][N:30]3[C:34](=[O:35])[C:33]([CH3:37])([CH3:36])[CH2:32][O:31]3)=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:10])=[O:11])[O:4][N:3]=1

Participants

7

Reactant 3

HCID 5238Sodium Iodide2×HCID 6397Chlorotrimethylsilane2×HCID 22103688HCID 22103688, compound

Product 1

HCID 22103664HCID 22103664, compoundYield 40.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

To a solution of the title compound of Step (A) (0.2 g, 0.327 mmol) in 4 mL of acetonitrile, chlorotrimethylsilane (0.213 g, 1.1 mmol) and sodium iodide (0.294 g, 1.965 mmol) were added the mixture stirred at room temperature for 30 min. Additional portions of chlorotrimethylsilane (0.12 g, 1.84 mmol) and sodium iodide (0.2 g, 1.33 mmol) were added over a 1 hr period and the mixture stirred for an additional 1 hr. The mixture was diluted with 25 mL of water and 1 mL of saturated aqueous sodium thiosulfate was added and the mixture was then extracted with 3×25 mL of EtOAc. The combined organic extracts were then washed once with water and dried and evaporated. The residue was purified by reverse phase preparative HPLC on a 30×500 mm ODS S10 column using 68% solvent B (90% MeOH, 10% H2O, 0.1% TFA) and 32% solvent A (10% MeOH, 90% H2O, 0.1% TFA). The appropriate fractions were collected and neutralized with aqueous sodium bicarbonate to pH 7 and concentrated to 10 mL. The solution was then acidified to pH 4 using aqueous sodium bisulfate and the white solid was filtered and dried to provide 0.069 g (40%) of the title compound of this Example as a white solid. m.p. 95°-100° C.

Workup

  1. stirringthe mixture stirred for an additional 1 hr
  2. additionwas added
  3. extractionthe mixture was then extracted with 3×25 mL of EtOAc
  4. washThe combined organic extracts were then washed once with water
  5. customdried
  6. customevaporated
  7. customThe residue was purified by reverse phase preparative HPLC on a 30×500 mm ODS S10 column
  8. customThe appropriate fractions were collected
  9. concentrationconcentrated to 10 mL
  10. filtrationthe white solid was filtered
  11. customdried

Sources & evidence

ORD record
ord-f6b724359ae942a5891607c45a037cb0
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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