Iodine → HCID 11540528, 화합물

HRID 2361628노트

반응식

HRID 2361628 반응식
[C:1]([O:4][C@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:24]=[CH:23][C:22](=[O:25])[NH:21][C:20]1=[O:26])(=[O:3])[CH3:2].[I:27]I.C(OCC)(=O)C.S(=O)(=O)(O)[O-].[Na+]>C(#N)C>[C:1]([O:4][C@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:24]=[C:23]([I:27])[C:22](=[O:25])[NH:21][C:20]1=[O:26])(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 807IodineHCID 8857Ethyl AcetateHCID 516919Sodium BisulfateHCID 12896718HCID 12896718, 화합물

생성물 1

HCID 11540528HCID 11540528, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

454 mg (1.23 mmol) of the above product 4 as starting material, 420 mg (1.66 mmol, 1.3 eq) of iodine and 700 mg (1.27 mmol, 1 eq) of ceric ammonium nitrate are dissolved in 15 mL of anhydrous acetonitrile and heated to 80° C. After the starting material disappears, 100 mL of ethyl acetate and 30 mL (5%) of sodium bisulfate are added in turns. 30 mL of saturated saline is used to wash. After collection and combination with an organic phase, the solution is concentrated by reduced pressure. After purified by rapid column chromatography (acetone/n-hexane=2:3), a white powder product (1-(2′,3′,5′-Tri-O-acetyl-β-D-arabinofuranosyl)-5-iodopyrimidin-2,4(3H)-dione) 5 is obtained. Its weight and yield are 425 mg and 70% respectively.

후처리

  1. washto wash
  2. customAfter collection and combination with an organic phase
  3. concentrationthe solution is concentrated by reduced pressure
  4. customAfter purified by rapid column chromatography (acetone/n-hexane=2:3)

출처 및 근거

ORD 기록
ord-183b3ce4bf9d43fdb3502795b12b9e32
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691789B2

반응 노트

불러오는 중…