Chloroform → HCID 90402322, 화합물

HRID 576708

반응식

HRID 576708 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 90402322HCID 90402322, 화합물수율 63.4%

시약·촉매·용매 2

HCID 16211523Ruthenium dioxide hydrate촉매3회HCID 962Water용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0f2b763345344f99945c83526da9f430
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040534B2

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