Acetic Anhydride → HCID 136005782, compound

HRID 915920Notes

Reaction equation

HRID 915920 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:24])[C:11]3[N:16]([CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)[N:15]=[C:14]([CH3:23])[C:12]=3[N:13]=2)=[CH:4][CH:3]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[CH:17]1([N:16]2[C:11]3[C:10](=[O:24])[NH:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([NH:1][C:25](=[O:27])[CH3:26])=[CH:3][CH:4]=4)=[N:13][C:12]=3[C:14]([CH3:23])=[N:15]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 136005863HCID 136005863, compound

Product 1

HCID 136005782HCID 136005782, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a 4 ml pyridine solution of 110 mg (0.34 mmol) of the compound obtained in Example 3, 39 μl (0.41 mmol) of acetic anhydride was added with ice cooling. The mixture was stirred at the same temperature for 30 minutes. Then, an aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. Then, the washed layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by recrystallization (ethanol) to obtain 43.7 mg (35%) of the captioned compound.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialThen, the washed layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by recrystallization (ethanol)

Sources & evidence

ORD record
ord-593dafdbe3c94e6db1f801437512b8ea
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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