Hydrogen chloride-ethyl acetate → HCID 23156153, compound

HRID 1890642Notes

Reaction equation

HRID 1890642 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]3[C:26]4=[N:27][C:28]([CH3:32])=[CH:29][C:30]([CH3:31])=[C:25]4[N:24]=[C:23]3[CH2:33][CH3:34])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(OCC)(=O)C.Cl>C(Cl)(Cl)Cl>[CH2:33]([C:23]1[N:22]([CH2:21][C:18]2[CH:19]=[CH:20][C:15]([NH:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:16][CH:17]=2)[C:26]2=[N:27][C:28]([CH3:32])=[CH:29][C:30]([CH3:31])=[C:25]2[N:24]=1)[CH3:34]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 69432942HCID 69432942, compound

Product 1

HCID 23156153HCID 23156153, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of Compound 105 (1.44 g, 3.11 mmol) in chloroform (12 mL) was added with a 4 mol/L hydrogen chloride-ethyl acetate solution (9.0 mL), followed by stirring at room temperature for 1.5 hours. After the reaction mixture was concentrated under reduced pressure, the residue was added with a 2 mol/L aqueous sodium hydroxide solution to control the pH to 12, and the mixture was extracted with chloroform three times. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained crystals were added with diisopropyl ether followed by stirring for 30 minutes, then the crystals were collected by filtration. The crystals were dried under reduced pressure to obtain Compound 140 (0.864 g, 2.38 mmol, 76%).

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. additionthe residue was added with a 2 mol/L aqueous sodium hydroxide solution
  3. extractionthe mixture was extracted with chloroform three times
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe obtained crystals were added with diisopropyl ether
  7. stirringby stirring for 30 minutes
  8. filtrationthe crystals were collected by filtration
  9. customThe crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-b19ab168cb0145388b1ff14bedbe5392
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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