Tetrahydrofuran → HCID 21714059, compound

HRID 650244Notes

Reaction equation

HRID 650244 reaction equation
C([N:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][N:7]=[C:6]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:5]1=[O:24])C=C.C[N+]1([O-])CC[O:29]CC1.[O:33]1[CH2:37][CH2:36][CH2:35]C1>C(OCC)(=O)C.C(Cl)(Cl)Cl.CO.[Os](=O)(=O)(=O)=O>[C:20]([O:19][C:17]([NH:16][C:6]1[C:5](=[O:24])[N:4]([CH2:35][CH:36]([OH:29])[CH2:37][OH:33])[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][N:7]=1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 21714048HCID 21714048, compound

Product 1

HCID 21714059HCID 21714059, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolventHCID 21584188Chloroform methanolSolvent

Procedure

4-Allyl-2-t-butyloxycarbonylamino-3-oxo-5-phenyl-3,4-dihydropyrazine (850 mg, 2.60 mmol) was dissolved in tetrahydrofuran (10.4 ml), and 4-methylmorpholine N-oxide (1.22 ml, 5.19 mmol) and 4% aqueous osmium tetroxide (0.83 mol. 0.13 mmol) was added to it, and the mixture was stirred overnight at room temperature. The reaction solution was diluted with ethyl acetate and then washed successively with saturated aqueous sodium thiosulfate, distilled water and saturated saline. The organic layer was dried over anhydrous magnesium sulfate, and the drying agent was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform/methanol=50/1) whereby title compound (750 mg, 80% yield) was obtained.

Workup

  1. washwashed successively with saturated aqueous sodium thiosulfate
  2. distillationdistilled water and saturated saline
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ca8b04212fd143abaf93363987468de4
Source dataset
uspto-grants-2001_08
Patent number
US06271238B1

Reaction notes

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