Trifluoroacetic acid → HCID 23121942, compound

HRID 1713546Notes

Reaction equation

HRID 1713546 reaction equation
[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])C)=[O:12])[CH2:10][CH:5]2[CH:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:3]1.FC(F)(F)C(O)=O.C(N(CC)CC)C.C(Cl)(=O)O[C:40]1[CH:45]=CC=C[CH:41]=1>ClCCl.C(OCC)(=O)C.O1CCCC1>[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]3[CH:16]=[CH:45][CH:40]=[CH:41][CH:17]=3)=[O:12])[CH2:10][CH:5]2[CH:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:3]1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 23121838HCID 23121838, compound

Product 1

HCID 23121942HCID 23121942, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,1-dimethylethyl tetrahydro-3-oxo-1-phenyl-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate (0.12 g, 0.38 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (1 mL), and the mixture was stirred at room temperature for 4 hours. The reaction solution was concentrated, and then ethyl acetate was added to the residue. 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 were added tetrahydrofuran (5 mL), triethylamine (0.10 ml, 0.75 mmol) and phenyl chlorocarbonate (88 mg, 0.56 mmol), 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 magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=9:1 to ethyl acetate) to obtain the title compound (0.10 g, yield 80%) as a diastereomer mixture. Diastereomer ratio (α:β=3:1).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionethyl acetate was added to the residue
  3. washThe resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. stirringthe mixture was stirred at room temperature for 2 hours
  7. washthe resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=9:1 to ethyl acetate)

Sources & evidence

ORD record
ord-323905ac549a4ac4ba2f5cfa823cd3a9
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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