Hydrogen chloride-ethyl acetate → HCID 68429551, compound

HRID 2191286Notes

Reaction equation

HRID 2191286 reaction equation
[CH3:1][C@@H:2]([O:6][C:7]1[CH:8]=[CH:9][C:10]2[CH2:11][N:12](C(OC(C)(C)C)=O)[CH2:13][CH2:14][O:15][C:16]=2[N:17]=1)[CH:3]([CH3:5])[CH3:4].[ClH:25].C(OCC)(=O)C>>[ClH:25].[CH3:1][C@@H:2]([O:6][C:7]1[CH:8]=[CH:9][C:10]2[CH2:11][NH:12][CH2:13][CH2:14][O:15][C:16]=2[N:17]=1)[CH:3]([CH3:4])[CH3:5]

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 68429497HCID 68429497, compound

Product 1

HCID 68429551HCID 68429551, compoundYield 78%

Procedure

A mixture of the compound obtained in step 1 (0.77 g) and 4N hydrogen chloride/ethyl acetate (10 mL) was stirred at room temperature for 3 hr. The precipitate was collected by filtration, and the aqueous layer was basified and extracted with ethyl acetate and aqueous sodium hydroxide solution. The organic layer was washed with saturated brine and dried, and the solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue, and 4N hydrogen chloride/ethyl acetate was added. The precipitate was collected by filtration and recrystallized twice from ethanol-diisopropyl ether to give the title compound (0.48 g, 78%) as a white powder.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. extractionextracted with ethyl acetate and aqueous sodium hydroxide solution
  3. washThe organic layer was washed with saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. additionEthyl acetate was added to the residue, and 4N hydrogen chloride/ethyl acetate
  7. additionwas added
  8. filtrationThe precipitate was collected by filtration
  9. customrecrystallized twice from ethanol-diisopropyl ether

Sources & evidence

ORD record
ord-6e4b650802084daa80b86edae27abc90
Source dataset
uspto-grants-2012_12
Patent number
US08329687B2

Reaction notes

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