Hydrogen chloride-ethyl acetate → HCID 178437436, compound

HRID 1890641Notes

Reaction equation

HRID 1890641 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C@H:16]2[CH2:21][CH2:20][C@H:19]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][N:30]4[C:34]5=[N:35][C:36]([CH3:40])=[CH:37][C:38]([CH3:39])=[C:33]5[N:32]=[C:31]4[CH2:41][CH3:42])=[CH:25][CH:24]=3)[CH2:18][CH2:17]2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(OCC)(=O)C.Cl>C(Cl)(Cl)Cl>[CH2:41]([C:31]1[N:30]([CH2:29][C:26]2[CH:25]=[CH:24][C:23]([NH:22][C@H:19]3[CH2:18][CH2:17][C@H:16]([C:14]([N:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)=[O:15])[CH2:21][CH2:20]3)=[CH:28][CH:27]=2)[C:34]2=[N:35][C:36]([CH3:40])=[CH:37][C:38]([CH3:39])=[C:33]2[N:32]=1)[CH3:42]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 178437438HCID 178437438, compound

Product 1

HCID 178437436HCID 178437436, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Compound 113 (261 mg, 0.454 mmol) was dissolved in chloroform (1.7 mL), and a 4 mol/L hydrogen chloride-ethyl acetate solution (4.5 mL) was added to the solution, followed by stirring at 0° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was added with a 2 mol/L aqueous sodium hydroxide solution, then extracted with ethyl acetate three times. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was recrystallized from ethanol-diisopropyl ether (1:20) to obtain Compound 114 (201 mg, 0.423 mmol, 93.3%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was added with a 2 mol/L aqueous sodium hydroxide solution
  3. extractionextracted with ethyl acetate three times
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from ethanol-diisopropyl ether (1:20)

Sources & evidence

ORD record
ord-a56ed2e03cfa4405afc64be87c710a1d
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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