Sodium Chloride → HCID 67282069, compound

HRID 2387742Notes

Reaction equation

HRID 2387742 reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.CS(Cl)(=O)=O.[F:13][C:14]1[CH:15]=[CH:16][C:17]([O:22][CH2:23][O:24][CH3:25])=[C:18](CO)[CH:19]=1.[Cl-].[Na+]>ClCCl>[F:13][C:14]1[CH:15]=[CH:16][C:17]([O:22][CH2:23][O:24][CH3:25])=[C:18]([CH2:7][C:6]#[N:3])[CH:19]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53729251HCID 53729251, compound

Product 1

HCID 67282069HCID 67282069, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (5.95 ml) and methanesulfonyl chloride (2.42 ml) were added to a dichloromethane (60 ml) solution of the compound 324-2 (5.23 g), while the solution was stirred under cooling on ice. The obtained mixture was stirred at room temperature for 1 hour. A saturated sodium chloride aqueous solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The obtained residue was dissolved in dimethyl sulfoxide (30 ml). Sodium cyanide (2.09 g) and sodium iodide (851 mg) were added to the solution, and the obtained mixture was stirred at 90° C. for 3 hours. The temperature of the reaction solution was returned to room temperature. Thereafter, water was added to the reaction solution, and the mixture was extracted with diethyl ether. The obtained organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=1:0 to 4:1), so as to obtain the title compound (4.33 g).

Workup

  1. temperatureunder cooling on ice
  2. stirringThe obtained mixture was stirred at room temperature for 1 hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe obtained organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe obtained residue was dissolved in dimethyl sulfoxide (30 ml)
  7. additionSodium cyanide (2.09 g) and sodium iodide (851 mg) were added to the solution
  8. stirringthe obtained mixture was stirred at 90° C. for 3 hours
  9. customwas returned to room temperature
  10. additionThereafter, water was added to the reaction solution
  11. extractionthe mixture was extracted with diethyl ether
  12. dry with materialThe obtained organic layer was dried over magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=1:0 to 4:1)

Sources & evidence

ORD record
ord-519976d08ffb48e5a758e37ae7392043
Source dataset
uspto-grants-2012_09
Patent number
US08268848B2

Reaction notes

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