Trifluoroacetic acid → HCID 23121989, compound

HRID 1713545Notes

Reaction equation

HRID 1713545 reaction equation
[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13]C(C)(C)C)=O)[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.O1CCCC1.[F:36][C:37]1[CH:42]=[CH:41][C:40]([N:43]=C=O)=[CH:39][CH:38]=1>ClCCl>[F:36][C:37]1[CH:42]=[CH:41][C:40]([NH:43][C:11]([N:9]2[CH2:8][CH2:7][N:6]3[C:2](=[O:1])[O:3][CH:4]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:5]3[CH2:10]2)=[O:13])=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8028TetrahydrofuranHCID 709554-Fluorophenyl isocyanateHCID 23121838HCID 23121838, compound

Product 1

HCID 23121989HCID 23121989, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl tetrahydro-3-oxo-1-phenyl-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate (94 mg, 0.30 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (0.5 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 (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. To the residue were added tetrahydrofuran (5 mL) and 4-fluorophenyl isocyanate (0.10 g, 0.73 mmol), and the mixture was stirred at 50° C. for 1 hour. The reaction solution was concentrated, and then the residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate) to obtain the title compound (20 mg, yield 19%) 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 (50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. stirringthe mixture was stirred at 50° C. for 1 hour
  7. concentrationThe reaction solution was concentrated
  8. customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate)

Sources & evidence

ORD record
ord-454a6a78fb2c49c88c725149d4554566
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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