Chloroform → HCID 90402322、化合物

HRID 576708

反応式

HRID 576708 の反応式
[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C:5]2=[N:4][N:3]=1.C(Cl)(Cl)Cl.CC#N.I([O-])(=O)(=O)=[O:26].[Na+]>O.O.[Ru](=O)=O>[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:10](=[O:26])[C:5]2=[N:4][N:3]=1

参加物

7

反応物 4

HCID 6212ChloroformHCID 6342AcetonitrileHCID 17998723tert-Butyl 3-bromo-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylateHCID 23667635Sodium periodate

生成物 1

HCID 90402322HCID 90402322、化合物収率 63.4%

試薬・触媒・溶媒 2

HCID 16211523Ruthenium dioxide hydrate触媒3 回HCID 962Water溶媒2 回

実験手順

To a vigorously stirred solution of tert-butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate (1.0 g, 3.3 mmol) in 1:1 CHCl3:MeCN (25 mL) was added ruthenium (IV) oxide hydrate (65 mg, 0.43 mmol) and sodium metaperiodate (3.3 g, 15.5 mmol) in water (31 mL). After 1 h, additional ruthenium (IV) oxide hydrate (50 mg) was added. After another hour, a final portion of ruthenium (IV) oxide hydrate (30 mg) was added. Stirring was maintained for 30 minutes and then water was added. The entire mixture was extracted with CHCl3. The combined organic extracts were dried (Na2SO4), filtered, and concentrated to afford a green oil. Purification by chromatography (SiO2; hexanes—100% EtOAc) provided the desired product as a white solid (663 mg, 63%). MS (ESI): mass calcd. for C10H13BrN4O3, 316.0; m/z found, 317.0 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 4.41-4.28 (m, 2H), 4.26-4.22 (m, 2H), 1.58 (s, 9H).

後処理

  1. waitAfter another hour
  2. temperaturewas maintained for 30 minutes
  3. extractionThe entire mixture was extracted with CHCl3
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a green oil
  8. customPurification by chromatography (SiO2; hexanes—100% EtOAc)

出典と根拠

ORDレコード
ord-0f2b763345344f99945c83526da9f430
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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