Hydrochloric Acid → HCID 54256258, compound

HRID 2270559Notes

Reaction equation

HRID 2270559 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:18]([O:20][C:21]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23]Br)[CH3:19].Cl>CN(C)C=O>[C:12]([O:11][C:9]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:23][C:22]1[CH:25]=[CH:26][CH:27]=[C:28]([N+:29]([O-:31])=[O:30])[C:21]=1[O:20][CH2:18][CH3:19])=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 279800Di-tert-butyl IminodicarboxylateHCID 18331400HCID 18331400, compound

Product 1

HCID 54256258HCID 54256258, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of iminodicarboxylic acid di-t-butyl ester (3.23 g), dimethylformamide (50 ml) and sodium hydride (0.57 g) was stirred under ice cooling for 1 h and then a mixture of the compound (3.51 g) obtained in Example 417c and dimethylformamide (20 ml) was added under ice cooling. The reaction mixture was stirred at room temperature for 14 h and, after addition of 2 N HCl, subjected to extraction with ethyl acetate. The organic layer was washed with 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, ethyl acetate:n-hexane=1:9) to give 5.09 g of the titled compound (yield, 95%).

Workup

  1. additionwas added under ice cooling
  2. stirringThe reaction mixture was stirred at room temperature for 14 h
  3. extractionsubjected to extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent, ethyl acetate:n-hexane=1:9)

Sources & evidence

ORD record
ord-2ec38e6056214a9e87546112c7b5e163
Source dataset
uspto-grants-2001_12
Patent number
US06331553B1

Reaction notes

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