Acetic Acid → HCID 67103508, compound

HRID 2080747Notes

Reaction equation

HRID 2080747 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:19]=[CH:18][C:8]2[N:9]=[C:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[N:11]([CH3:12])[C:7]=2[CH:6]=1)=[O:4].[C:20](O)(=O)[CH3:21].[C:24]([BH3-])#N.[Na+].[CH:28](=O)[CH2:29][CH3:30]>CO>[CH3:1][O:2][C:3]([C:5]1[CH:19]=[CH:18][C:8]2[N:9]=[C:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:24][CH2:20][CH3:21])[CH2:28][CH2:29][CH3:30])[N:11]([CH3:12])[C:7]=2[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 5003444Sodium cyanoborohydrideHCID 67103837HCID 67103837, compound

Product 1

HCID 67103508HCID 67103508, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (219 mg) obtained in Example 13-2 was dissolved in methanol (4.2 ml). The solution was added with acetic acid (200 μl), sodium cyanoborohydride (170.9 mg), and gradually added with propionaldehyde (180 μl) and the whole was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. Then, the residue was dissolved in chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution, followed by extraction with chloroform. The organic layer was washed with a saturated saline solution and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, thereby obtaining the subject compound (305 mg) as a brown oily substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThen, the residue was dissolved in chloroform
  4. washwashed with a 1 mol/l sodium hydroxide aqueous solution
  5. extractionfollowed by extraction with chloroform
  6. washThe organic layer was washed with a saturated saline solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-86365c904abe4fb3b3c10492cec1ada5
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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