Water → HCID 90402284, compound

HRID 576728

Reaction equation

HRID 576728 reaction equation
[CH3:1][C@H:2]1[CH2:7][N:6]2[C:8]([C:11]3[CH:16]=[N:15][CH:14]=[CH:13][N:12]=3)=[N:9][N:10]=[C:5]2[CH2:4][N:3]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(#N)C.O.I([O-])(=O)(=O)=[O:29].[Na+]>C(Cl)(Cl)Cl.O.[Ru](=O)=O>[CH3:1][C@H:2]1[CH2:7][N:6]2[C:8]([C:11]3[CH:16]=[N:15][CH:14]=[CH:13][N:12]=3)=[N:9][N:10]=[C:5]2[C:4](=[O:29])[N:3]1[C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18]

Participants

7

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 23667635Sodium periodateHCID 90402323HCID 90402323, compound

Product 1

HCID 90402284HCID 90402284, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 16211523Ruthenium dioxide hydrateCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of (S)-tert-butyl 6-methyl-3-(pyrazin-2-yl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate (1.0 g, 3.2 mmol) in chloroform (12 mL) was added acetonitrile (12 mL), water (30 mL), sodium metaperiodate (3.2 g, 14.9 mmol) and ruthenium (IV) oxide hydrate (62 mg, 0.4 mmol) and the reaction mixture was vigorously stirred for 30 minutes. The reaction mixture was filtered through celite, extracted with DCM, the organic layers were washed with brine, dried with Na2SO4, filtered, concentrated and purified by flash column chromatography (0-100% EtOAc in hexanes) to provide the desired compound (0.50 g, 48%). 1H NMR (400 MHz, DMSO) δ 9.47 (s, 1H), 8.83 (s, 2H), 5.01-4.92 (m, 1H), 4.89-4.79 (m, 1H), 4.73-4.66 (m, 1H), 1.52 (s, 9H), 1.21 (d, J=6.8 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. extractionextracted with DCM
  3. washthe organic layers were washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bbda560bdc494c7ebfbdc40ecca4a45b
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Linked notes

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