Sodium Iodide → HCID 22103617, compound

HRID 1457213Notes

Reaction equation

HRID 1457213 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[CH:18]=[C:17]([C:19]2[O:20][CH:21]=[CH:22][N:23]=2)[CH:16]=[CH:15][C:14]=1[C:24]1[C:25]([S:30]([N:33]([C:40]2[O:44][N:43]=[C:42]([CH3:45])[C:41]=2[CH3:46])COCCOC)(=[O:32])=[O:31])=[CH:26][CH:27]=[CH:28][CH:29]=1.Cl[Si](C)(C)C.[I-].[Na+]>C(Cl)Cl.O>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][C:13]1[CH:18]=[C:17]([C:19]2[O:20][CH:21]=[CH:22][N:23]=2)[CH:16]=[CH:15][C:14]=1[C:24]1[C:25]([S:30]([NH:33][C:40]2[O:44][N:43]=[C:42]([CH3:45])[C:41]=2[CH3:46])(=[O:32])=[O:31])=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 5238Sodium Iodide2×HCID 6397Chlorotrimethylsilane2×HCID 22103648HCID 22103648, compound

Product 1

HCID 22103617HCID 22103617, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the title compound of Step (A) (0.05 g, 0.087 mmol) in 10 mL of CH2Cl2, chlorotrimethylsilane (0.019 g, 0.17 mmol) and sodium iodide (0.026 g, 0.17 mmol) were added the mixture stirred at room temperature for 2 hr. Additional portions of chlorotrimethylsilane (0.019 g, 0.17 mmol) and sodium iodide (0.026 g, 0.17 mmol) were added and the mixture stirred for an additional 1 hr. The mixture was diluted with 15 mL of water and extracted with 3×15 mL of CH2Cl2. 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 75% solvent B (90% MeOH, 10% H2O, 0.1% TFA) and 25% 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 0.026 g (54%) of the title compound of this Example as a white solid. m.p 120°-130° C.

Workup

  1. stirringthe mixture stirred for an additional 1 hr
  2. extractionextracted with 3×15 mL of CH2Cl2
  3. washThe combined organic extracts were then washed once with water
  4. customdried
  5. customevaporated
  6. customThe residue was purified by reverse phase preparative HPLC on a 30×500 mm ODS S10 column
  7. customThe appropriate fractions were collected
  8. concentrationconcentrated to 10 mL
  9. filtrationthe white solid was filtered
  10. customdried

Sources & evidence

ORD record
ord-78c8017d0342489abff67ad172eb94d6
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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