Water → HCID 16093681, compound

HRID 1244796Notes

Reaction equation

HRID 1244796 reaction equation
O.[CH2:2]([O:9][C:10]([N:12]([CH2:19][CH:20](OCC)[O:21]CC)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(Cl)(Cl)Cl.FC(F)(F)C(O)=O>[CH2:2]([O:9][C:10]([N:12]([CH2:19][CH:20]=[O:21])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 962Water2×HCID 16093664HCID 16093664, compound

Product 1

HCID 16093681HCID 16093681, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

After adding water (60 ml) to a solution of the compound obtained in Step 1 (14.1 g) in chloroform (120 ml), trifluoroacetic acid (153 ml) was added dropwise over 2 hours under cooling with ice. The mixture was stirred under cooling with ice for 1 hour and at room temperature for 1.5 hours. After adding water to the reaction mixture and extracting with methylene chloride, the organic layer was washed with aqueous solution of 10% potassium carbonate, water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled off under reduced pressure to obtain the title compound (10.3 g).

Workup

  1. additionwas added dropwise over 2 hours
  2. temperatureunder cooling with ice
  3. extractionextracting with methylene chloride
  4. washthe organic layer was washed with aqueous solution of 10% potassium carbonate, water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThereafter, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-56bd04c63b054cc9b5b3527409291253
Source dataset
uspto-grants-2006_10
Patent number
US07122662B2

Reaction notes

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