Iodine → 2',3'-Dideoxy-5-iodocytidine

HRID 1029374

반응식

HRID 1029374 반응식
[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

참가 물질

5

반응물 2

HCID 807IodineHCID 24066Dideoxycytidine

생성물 1

HCID 146301042',3'-Dideoxy-5-iodocytidine수율 83%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 6344Dichloromethane용매

실험 절차

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°).

후처리

  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

출처 및 근거

ORD 기록
ord-58c25d147f4c4516a02128e4ae8f433d
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05102785

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