Sodium Iodide → HCID 86709369, compound

HRID 2172184Notes

Reaction equation

HRID 2172184 reaction equation
[Cl:1][C:2]1[N:3]([CH2:10][CH2:11][C@@H:12]([OH:25])[CH2:13][O:14]S(C2C=CC(C)=CC=2)(=O)=O)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[Si:26]([O:33][CH:34]1[CH2:39][CH2:38][N:37]([CH:40]2[CH2:45][CH2:44][N:43]([C:46]3[CH:51]=[CH:50][C:49](O)=[CH:48][CH:47]=3)[CH2:42][CH2:41]2)[CH2:36][CH2:35]1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[I-].[Na+]>C(O)C>[Si:26]([O:33][CH:34]1[CH2:35][CH2:36][N:37]([CH:40]2[CH2:45][CH2:44][N:43]([C:46]3[CH:51]=[CH:50][C:49]([O:14][CH2:13][C@H:12]([OH:25])[CH2:11][CH2:10][N:3]4[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=[C:2]4[Cl:1])=[CH:48][CH:47]=3)[CH2:42][CH2:41]2)[CH2:38][CH2:39]1)([C:29]([CH3:32])([CH3:30])[CH3:31])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 62657Potassium Phosphate, TribasicHCID 86709368HCID 86709368, compoundHCID 86709370HCID 86709370, compound

Product 1

HCID 86709369HCID 86709369, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

Toluene-4-sulfonic acid (R)-4-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxybutyl ester (848 mg) and 4-[4-(tert-butyl-dimethylsilanyloxy)[1,4′]bipiperidinyl-1′-yl]phenol (850 mg) were suspended in ethanol (30 ml). Tripotassium phosphate (1.02 g) and sodium iodide (359 mg) were added to the suspension, and the mixture was stirred at 75° C. for 3 hours under a nitrogen atmosphere. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure, and water was added to the resulting residue, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. Insoluble matter that was precipitated by adding isopropyl ether to the residue was collected by filtration to afford the title compound as a pale brown powder (470 mg).

Workup

  1. temperatureAfter being cooled to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure, and water
  3. additionwas added to the resulting residue
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customInsoluble matter that was precipitated
  8. additionby adding isopropyl ether to the residue
  9. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-2d07d5f868b94b6d960ddae6cbf9ac86
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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