Triethylamine → HCID 86653949, compound

HRID 2088746Notes

Reaction equation

HRID 2088746 reaction equation
C(N(CC)CC)C.[F:8][C:9]([F:22])([F:21])[S:10]([O:13]S(C(F)(F)F)(=O)=O)(=[O:12])=[O:11].O[C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[N:28]([CH3:34])[C:27]2([CH3:36])[CH3:35].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[F:8][C:9]([F:22])([F:21])[S:10]([O:13][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[N:28]([CH3:34])[C:27]2([CH3:36])[CH3:35])(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 58289837HCID 58289837, compound

Product 1

HCID 86653949HCID 86653949, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

With cooling with ice, 0.192 mL of triethylamine and 0.174 mL of trifluoromethanesulfonic acid anhydride were added to 4.3 mL of a chloroform solution of 165 mg of 5-hydroxy-2,3,3-trimethylisoindolin-1-one obtained in Production Example 49-2, and stirred for 1 hour with cooling with ice. 2 mL of aqueous saturated sodium hydrogencarbonate solution was added to the reaction liquid, and extracted with chloroform. The organic layer was dried with anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The crude product was purified through silica gel column chromatography (chloroform) to obtain 257 mg of the entitled compound as a colorless solid.

Workup

  1. customobtained in Production Example 49-2
  2. temperaturewith cooling with ice
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. customthe solvent was evaporated away under reduced pressure
  6. customThe crude product was purified through silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-60ccdab4953a417a8a0c593a4484d286
Source dataset
uspto-grants-2013_05
Patent number
US08436004B2

Reaction notes

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