Potassium Iodide → HCID 86586594, compound

HRID 1837604Notes

Reaction equation

HRID 1837604 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:22][OH:23])[CH2:10][CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N([CH2:29][CH3:30])CC)C.S(Cl)(C)(=O)=O.[Cl-].[Li+].O[C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][C:46]=1I)C#N.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>ClCCl.CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:22][O:23][C:39]1[CH:40]=[CH:41][CH:44]=[C:45]([CH:29]=[CH2:30])[CH:46]=1)[CH2:10][CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

10

Reactant 7

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 109446813-Hydroxy-4-iodobenzonitrileHCID 11198087HCID 11198087, compound

Product 1

HCID 86586594HCID 86586594, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

11.25 g (34.8 mmol) of benzyl (4S)-4-((t-butoxycarbonyl)amino)-5-hydroxypentanoate acid obtained in step 1 was dissolved in 120 ml of dichloromethane. 9.7 ml (69.6 mmol) of triethylamine was added to the obtained solution. 6.0 ml (52.2 mmol) of mesyl chloride was added to the obtained mixture at 0° C., and they were stirred at room temperature for 4 hours. The solvent was evaporated, and the residue was treated with ethyl acetate as the extracting solvent by an ordinary method to obtain the crude product. This crude product was dissolved in 100 ml of N,N-dimethylformamide (dehydrated). 7.4 g (174 mmol) of lithium chloride was added to the obtained solution, and they were stirred at 50° C. for 6 hours. The solvent was evaporated, and the residue was treated with ethyl acetate as the extracting solvent by an ordinary method to obtain the crude product, which was dissolved in 150 ml of N,N-dimethylformamide (dehydrated). 6.8 g (27.7 mmol) of 3-hydroxy-4-iodobenzonitrile, 5.73 g (41.5 mmol) of potassium carbonate and 4.6 g (27.7 mmol) of potassium iodide were added to the obtained solution, and they were stirred at 90° C. overnight. The solvent was evaporated, and the residue was treated with ethyl acetate as the extracting solvent by an ordinary method to obtain the crude product, which was then purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was treated with ethyl acetate as the extracting solvent by an ordinary method
  3. customto obtain the crude product
  4. stirringwere stirred at 50° C. for 6 hours
  5. customThe solvent was evaporated
  6. additionthe residue was treated with ethyl acetate as the extracting solvent by an ordinary method
  7. customto obtain the crude product, which
  8. stirringwere stirred at 90° C. overnight
  9. customThe solvent was evaporated
  10. additionthe residue was treated with ethyl acetate as the extracting solvent by an ordinary method
  11. customto obtain the crude product, which
  12. customwas then purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-97d1ff4fc44d462dadbb6ba5ffb4a918
Source dataset
uspto-grants-2004_08
Patent number
US06784191B2

Reaction notes

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