Imidazole → HCID 22853609, 화합물

HRID 37062

반응식

HRID 37062 반응식
[F:1][C:2]1[C:3](=[O:18])[NH:4][C:5](=[O:17])[N:6]([CH:16]=1)[C@@H:7]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]1[OH:9].N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].O>CN(C)C=O.CO.C(Cl)(Cl)Cl>[Si:24]([O:14][CH2:13][C@H:12]1[O:15][C@@H:7]([N:6]2[CH:16]=[C:2]([F:1])[C:3](=[O:18])[NH:4][C:5]2=[O:17])[C@H:8]([OH:9])[C@@H:10]1[OH:11])([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

참가 물질

8

반응물 4

HCID 795ImidazoleHCID 962WaterHCID 94275-FluorouridineHCID 28928tert-Butyldimethylsilyl chloride

생성물 1

HCID 22853609HCID 22853609, 화합물수율 82.2%

시약·촉매·용매 3

HCID 887Methanol용매HCID 6212Chloroform용매HCID 6228Dimethylformamide용매

실험 절차

A 1.50 g quantity of 5-fluorouridine (5.72 mmoles) was dissolved in 5 ml of N,N-dimethylformamide. To the solution were added 520 mg (7.64 mmoles) of imidazole and 633 mg (4.20 mmoles) of tert-butyldimethylsilyl chloride, and the reaction was conducted at room temperature for 15 hours. -The reaction mixture was ice-cooled, and 40 ml of water was added thereto. The reaction mixture was extracted three times with 40 ml of ethyl acetate. The organic layers were combined, washed three times with 50 ml of water and washed three times with 50 ml of a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue thus obtained was subjected to silica gel column chromatography (chloroform: methanol=20:1). The eluate was concentrated and the residue was recrystallized from ether, giving 1.3 g of the title compound as white crystals. Yield: 60%.

후처리

  1. custom-The reaction mixture
  2. temperaturecooled
  3. extractionThe reaction mixture was extracted three times with 40 ml of ethyl acetate
  4. washwashed three times with 50 ml of water
  5. washwashed three times with 50 ml of a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated off under reduced pressure
  8. customthe residue thus obtained
  9. concentrationThe eluate was concentrated
  10. customthe residue was recrystallized from ether

출처 및 근거

ORD 기록
ord-647c5c1d4cb64e2bb484b37acbde21c0
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420117

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