Potassium Iodide → HCID 16086063, compound

HRID 394036Notes

Reaction equation

HRID 394036 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7](=[O:31])[CH2:8][C:9]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C@H:4]([C:32]([N:34]2[CH2:38][CH2:37][CH2:36][C@@H:35]2[C:39]([NH:41][CH2:42][CH:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)=[O:40])=[O:33])[CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:57](#N)[CH3:58]>C(Cl)(Cl)Cl>[CH:57]1([CH2:58][N:46]2[CH2:45][CH2:44][CH:43]([CH2:42][NH:41][C:39]([C@H:35]3[CH2:36][CH2:37][CH2:38][N:34]3[C:32]([C@@H:4]3[CH2:3][C@@H:2]([OH:1])[CH2:6][N:5]3[C:7](=[O:31])[CH2:8][C:9]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[O:33])=[O:40])[CH2:48][CH2:47]2)[CH2:4][CH2:3][CH2:2][CH2:6]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 16086059HCID 16086059, compound

Product 1

HCID 16086063HCID 16086063, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 19 mg of (2R)-1-((2S,4R)-4-hydroxy-1-{3,3,3-tris(4-fluorophenyl)propanoyl}pyrrolidin-2-yl)carbonyl-N-(4-piperidylmethyl)pyrrolidine-2-carboxamide in 1.5 ml of acetonitrile, 14 mg of methanesulfonic acid-cyclopentylmethyl, 13 mg of potassium carbonate and 5 mg of potassium iodide were added at room temperature, followed by 24 hours' stirring at 80° C. under heating. The reaction liquid was diluted with chloroform, washed successively with water and 1N aqueous sodium hydroxide solution, and drired over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, the resultant residue was purified by preparative thin-layer chromatography [Kieselgel™ 60F254, Art 5744 (Merck), chloroform/methanol/28% aqueous ammonia=100/10/1) to provide 16 mg of the title compound as a white solid.

Workup

  1. temperatureunder heating
  2. customThe reaction liquid
  3. washwashed successively with water and 1N aqueous sodium hydroxide solution
  4. distillationDistilling the solvent off under reduced pressure
  5. customthe resultant residue was purified by preparative thin-layer chromatography [Kieselgel™ 60F254, Art 5744 (Merck), chloroform/methanol/28% aqueous ammonia=100/10/1)

Sources & evidence

ORD record
ord-8e05d17810704b4397bc9aa88fc4f1f3
Source dataset
uspto-grants-2004_10
Patent number
US06809108B1

Reaction notes

Loading…