Iodine → HCID 178455352, compound

HRID 1913525Notes

Reaction equation

HRID 1913525 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH:19]=[C:18]([CH2:20][OH:21])[N:17]=[CH:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].II.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.O>[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH:19]=[C:18]([CH:20]=[O:21])[N:17]=[CH:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 178455353HCID 178455353, compound

Product 1

HCID 178455352HCID 178455352, compoundYield 99.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

The compound (260 mg) obtained in Step 1 of this Reference Example was dissolved in toluene (10 mL) and methylene chloride (1 mL). To the solution, a solution of sodium bicarbonate (210 mg, 2.50 mmol) in water (8 mL), iodine (370 mg), and 2,2,6,6-tetramethyl-1-piperidinyloxy (15 mg) were added in this order, and the mixture was stirred at room temperature for 12 hours. To the reaction solution, saturated aqueous sodium thiosulfate was added, and organic matter was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. This crude product was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=2/1-1/1) to obtain the title compound (258 mg).

Workup

  1. extractionorganic matter was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto obtain a crude product
  6. customThis crude product was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=2/1-1/1)

Sources & evidence

ORD record
ord-bdd09e6d5e7b4d2fb3b12fa476094863
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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