碘 → 2',3'-Dideoxy-5-iodocytidine

HRID 1029374

反应方程式

HRID 1029374 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 hours. 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°. After 4 hours, the free base form of AG3 X4A resin (20 mL, 38 meq, Bio-Rad) was added and hydrogen sulfide was bubbled into the reaction for 15 minutes. Complete precipitation of mercury(II) was verified by TLC. The reaction was filtered through 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 19 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. additionthe free base form of AG3 X4A resin (20 mL, 38 meq, Bio-Rad) was added
  2. customhydrogen sulfide was bubbled into the reaction for 15 minutes
  3. customComplete precipitation of mercury(II)
  4. filtrationThe reaction was filtered
  5. filtrationthrough filter aid
  6. washthe filter aid was washed with 1:1 methanol-dichloromethane
  7. customThe filtrate was evaporated onto silica gel (10 g)
  8. washElution with 5%, 10% and 20% methanol in dichloromethane

来源与证据

ORD记录
ord-58c25d147f4c4516a02128e4ae8f433d
来源数据集
uspto-grants-1992_04
专利号
US05102785

关联笔记

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