Iodine → HCID 11540528、化合物

HRID 2361628ノート

反応式

HRID 2361628 の反応式
[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]

参加物

6

反応物 4

HCID 807IodineHCID 8857Ethyl AcetateHCID 516919Sodium BisulfateHCID 12896718HCID 12896718、化合物

生成物 1

HCID 11540528HCID 11540528、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-183b3ce4bf9d43fdb3502795b12b9e32
出典データセット
uspto-grants-2014_04
特許番号
US08691789B2

反応ノート

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