Acetaldehyde → HCID 23121872, compound

HRID 1713570Notes

Reaction equation

HRID 1713570 reaction equation
[ClH:1].[O:2]=[C:3]1[N:7]2[CH2:8][CH2:9][N:10]([C:12]([NH:14][CH2:15][CH2:16][NH:17][CH2:18][CH:19]=[CH2:20])=[O:13])[CH2:11][CH:6]2[C:5]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:4]1.C(=O)([O-])O.[Na+].[CH:38](=O)[CH3:39].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(OCC)(=O)C>[ClH:1].[CH2:38]([N:17]([CH2:18][CH:19]=[CH2:20])[CH2:16][CH2:15][NH:14][C:12]([N:10]1[CH2:9][CH2:8][N:7]2[C:3](=[O:2])[O:4][C:5]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:6]2[CH2:11]1)=[O:13])[CH3:39]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 23121875HCID 23121875, compound

Product 1

HCID 23121872HCID 23121872, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To tetrahydro-3-oxo-1,1-diphenyl-N-[2-[(2-propenyl)amino]ethyl]-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxamide hydrochloride (0.13 g, 0.29 mmol) was added a 0.5 M aqueous sodium hydrogen carbonate solution (20 mL), and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in a 1,2-dichloroethane solution (5 mL). Acetaldehyde (25 mg, 0.57 mmol) and sodium triacetoxyborohydride (0.12 g, 0.57 mmol) were sequentially added thereto, and the mixture was stirred at room temperature for 8 hours. To the reaction solution was added ethyl acetate, and the resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. To the residue was added a 4M hydrogen chloride/ethyl acetate solution (1.0 mL), and the mixture was stirred at room temperature for 10 minutes. The reaction solution was concentrated under reduced pressure, and then the residue formed powder from 2-propanol-ethyl acetate to obtain the title compound (77 mg, yield 56%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in a 1,2-dichloroethane solution (5 mL)
  5. washthe resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionTo the residue was added a 4M hydrogen chloride/ethyl acetate solution (1.0 mL)
  9. stirringthe mixture was stirred at room temperature for 10 minutes
  10. concentrationThe reaction solution was concentrated under reduced pressure
  11. customthe residue formed powder from 2-propanol-ethyl acetate

Sources & evidence

ORD record
ord-2c86651dbbad4f2989b27638b12242bd
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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