Water → HCID 90402284, 화합물

HRID 576728

반응식

HRID 576728 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 90402284HCID 90402284, 화합물수율 48%

시약·촉매·용매 2

HCID 16211523Ruthenium dioxide hydrate촉매HCID 6212Chloroform용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-bbda560bdc494c7ebfbdc40ecca4a45b
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040534B2

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