碘 → 2',3'-Dideoxy-5-iodocytidine

HRID 728221

反应方程式

HRID 728221 反应方程式
[C@@H:1]1([N:8]2[CH:15]=[CH:14][C:12]([NH2:13])=[N:11][C:9]2=[O:10])[O:7][C@H:4]([CH2:5][OH:6])[CH2:3][CH2:2]1.[I:16]I>CO.ClCCl>[I:16][C:14]1[C:12]([NH2:13])=[N:11][C:9](=[O:10])[N:8]([CH:15]=1)[C@@H:1]1[O:7][C@H:4]([CH2:5][OH:6])[CH2:3][CH2:2]1

参与物

5

反应物 2

HCID 807碘HCID 24066Dideoxycytidine

产物 1

HCID 146301042',3'-Dideoxy-5-iodocytidine收率 83%

试剂、催化剂与溶剂 2

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂2 次HCID 6344二氯甲烷溶剂

实验过程

A solution of 2',3'-dideoxycytidine (2.11 g, 10 mmol, Raylo) and mercuric acetate (3.35 g, 10.5 mmol, Fisher) in 50 mL of methanol was refluxed for 19 h. The resulting white suspension was diluted with methanol (50 mL) and dichloromethane (100 mL). Iodine (3.05 g, 12 mmol) was added and the suspension was stirred at 25° until a clear purple solution was present After 4 h, the free base form of AG3 X4A resin (20 mL, 38 meq, Bio-Rad; a weakly basic polystyrene resin) was added and hydrogen sulfide was bubbled into the reaction for 15 min. Complete precipitation of mercury(II) was verified by TLC. The reaction was filtered though filter aid and the filter aid was washed with 1:1 methanol-dichloromethane. The filtrate was evaporated onto silica gel (10 g) and the loaded silica gel was placed on top of a 150 g silica gel column. Elution with 5%, 10% and 20% methanol in dichloromethane afforded 2.79 g (83%) of iodide 44 as a colorless crystalline solid. Two recrystallizations from boiling water afforded, after vacuum-drying at 50°, large, analytically-pure prisms (mp: d 178°).

后处理

  1. customhydrogen sulfide was bubbled into the reaction for 15 min
  2. customprecipitation of mercury(II)
  3. filtrationThe reaction was filtered
  4. filtrationthough filter aid
  5. washthe filter aid was washed with 1:1 methanol-dichloromethane
  6. customThe filtrate was evaporated onto silica gel (10 g)
  7. washElution with 5%, 10% and 20% methanol in dichloromethane

来源与证据

ORD记录
ord-ac7e84dac8b9447eb25aa0c93dbec33a
来源数据集
uspto-grants-1991_09
专利号
US05047519

关联笔记

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