Hydrochloric Acid → HCID 22981233, compound

HRID 1861922Notes

Reaction equation

HRID 1861922 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[CH2:12][N:13]1[C:17](=[O:18])C2=CC=CC=C2C1=O.[OH2:24].NN.Cl>CO>[C:4]([O:24][C:17](=[O:18])[NH:13][CH2:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])([CH3:12])([CH3:5])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 18621716HCID 18621716, compound

Product 1

HCID 22981233HCID 22981233, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of the compound (357 mg) obtained in Example 117 and methanol (10 ml), hydrazine monohydrate (0.06 ml) was added and stirred at room temperature for 3 h. The reaction mixture was made acidic by addition of 2 N HCl and washed with ethyl acetate. The aqueous layer was made alkaline by addition of a 2 N aqueous sodium hydroxide solution and extracted with ethyl acetate; then, the organic layer was washed successively with water and a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. To a solution of the resulting residue in dimethylformamide (10 ml), di-t-butyl dicarbonate (274 mg) and triethylamine (0.17 ml) were added and stirred at room temperature for 3 h. Water and 2 N HCl were added to the reaction mixture and extraction was performed with ethyl acetate; then, the organic layer was washed successively with water and a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=1:1) to give 62 mg of the titled compound (yield, 20%).

Workup

  1. additionwas added
  2. washwashed with ethyl acetate
  3. additionby addition of a 2 N aqueous sodium hydroxide solution
  4. extractionextracted with ethyl acetate
  5. washthen, the organic layer was washed successively with water
  6. dry with materiala saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionTo a solution of the resulting residue in dimethylformamide (10 ml), di-t-butyl dicarbonate (274 mg) and triethylamine (0.17 ml) were added
  9. stirringstirred at room temperature for 3 h
  10. additionWater and 2 N HCl were added to the reaction mixture and extraction
  11. washthen, the organic layer was washed successively with water
  12. dry with materiala saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-3b759288ce2a48b282f69941be187584
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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