Hydrochloric Acid → HCID 86662652, compound

HRID 406343Notes

Reaction equation

HRID 406343 reaction equation
[C:1]([O:5][C:6]([NH:8][NH:9][CH:10]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1)[CH2:11][CH2:12][CH2:13][C:14](OCC)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl.C(OCC)(=O)C>CO>[O:15]=[C:14]1[CH2:13][CH2:12][CH2:11][CH:10]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[N:9]1[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 66777612HCID 66777612, compound

Product 1

HCID 86662652HCID 86662652, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 5-(N′-tert-butoxycarbonylhydrazino)-5-(3-trifluoromethylphenyl)pentanoate (323 mg) was dissolved in methanol (7 mL). A 1 N sodium hydroxide solution (5 mL) was added and the mixture was stirred at room temperature for two hours and 30 minutes. 1 N hydrochloric acid (5 mL) and ethyl acetate were added to the reaction solution, and the organic layer was separated and dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the organic layer was concentrated under reduced pressure. The residue was dissolved in dimethylformamide (8 mL). 1-Ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (317 mg) and 1-hydroxybenzotriazole (223 mg) were added and the mixture was stirred at room temperature for 13 hours. 1-Ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (317 mg) was added to the reaction solution, and the mixture was further stirred for one hour. Diethyl ether and water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (214 mg). The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe drying agent was separated by filtration
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in dimethylformamide (8 mL)
  6. addition1-Ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (317 mg) and 1-hydroxybenzotriazole (223 mg) were added
  7. stirringthe mixture was stirred at room temperature for 13 hours
  8. addition1-Ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (317 mg) was added to the reaction solution
  9. stirringthe mixture was further stirred for one hour
  10. additionDiethyl ether and water were added to the reaction solution
  11. customthe organic layer was separated
  12. washThe resulting organic layer was washed with brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. customThe drying agent was separated by filtration
  15. concentrationthe organic layer was concentrated under reduced pressure
  16. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8abec7196af74bb2b4fbdebf695ed14e
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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