Acetic Anhydride → HCID 23121882, compound

HRID 1713569Notes

Reaction equation

HRID 1713569 reaction equation
Cl.[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+].C(N(CC)CC)C.[C:45](OC(=O)C)(=[O:47])[CH3:46]>C(OCC)(=O)C>[C:45]([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])(=[O:47])[CH3:46]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 23121875HCID 23121875, compound

Product 1

HCID 23121882HCID 23121882, compoundYield 68%

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 tetrahydrofuran (5 mL). Triethylamine (58 mg, 0.57 mmol) and acetic anhydride (32 mg, 0.31 mmol) were sequentially added thereto, and the mixture was stirred at room temperature for 2 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. The residue was recrystallized from diisopropyl ether to obtain the title compound (90 mg, yield 68%).

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 tetrahydrofuran (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. customThe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-2aeba3d2ac3448f2b472494176cbbb0f
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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