Water → HCID 90402284、化合物

HRID 576728

反応式

HRID 576728 の反応式
[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]

参加物

7

反応物 4

HCID 962WaterHCID 6342AcetonitrileHCID 23667635Sodium periodateHCID 90402323HCID 90402323、化合物

生成物 1

HCID 90402284HCID 90402284、化合物収率 48%

試薬・触媒・溶媒 2

HCID 16211523Ruthenium dioxide hydrate触媒HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bbda560bdc494c7ebfbdc40ecca4a45b
出典データセット
uspto-grants-2015_05
特許番号
US09040534B2

関連ノート

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