Trimethylsilyl triflate → HCID 10746734, 화합물

HRID 2186324노트

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HRID 2186324 반응식
[CH2:1]([Si:3]([C:8]#[C:9][C@:10]1([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:18][CH:13](OC(=O)C)[C@H:12]([O:19][C:20](=[O:22])[CH3:21])[C@@H:11]1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].N[C:41]1[NH:49][C:48]2[C:43](=[N:44][C:45]([NH2:50])=[N:46][CH:47]=2)[N:42]=1.C/C(/O[Si](C)(C)C)=[N:53]\[Si](C)(C)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C(=O)([O-])O.[Na+]>ClCCCl>[C:20]([O:19][C@@H:12]1[C@H:11]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@:10]([C:9]#[C:8][Si:3]([CH2:4][CH3:5])([CH2:6][CH3:7])[CH2:1][CH3:2])([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:18][C@H:13]1[N:42]1[CH:41]=[N:49][C:48]2[C:43]1=[N:44][C:45]([NH2:50])=[N:46][C:47]=2[NH2:53])(=[O:22])[CH3:21]

참가 물질

7

반응물 5

HCID 65367Trimethylsilyl triflateHCID 2439487h-purine-2,8-diamineHCID 516892Sodium BicarbonateHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 12042250HCID 12042250, 화합물

생성물 1

HCID 10746734HCID 10746734, 화합물

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of Compound 6 (1.1 g, 2 mmol) in 1,2-dichloroethane (16.5 ml), diaminopurine (0.45 g, 3 mmol) and N,O-bis(trimethylsilyl)acetamide (4.4 ml, 18 mmol) were added, followed by refluxing for three hours. After the mixture was cooled to room temperature, trimethylsilyl trifluoromethanesulfonate (0.77 ml, 4 mmol) was added dropwise to the mixture at 0° C. in an argon atmosphere. The mixture was stirred for 15 minutes at room temperature, refluxed for 24 hours, and cooled to room temperature. A saturated aqueous solution of sodium hydrogencarbonate was added thereto at 0° C., followed by stirring for 15 minutes at room temperature. Insoluble materials were separated through filtration by use of Celite, and then the organic layer was separated from the filtrate. After an aqueous layer was extracted with chloroform once, the organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was applied to a silica gel column (20 g, eluent; ethyl acetate:n-hexane:ethanol=20:10:1), to thereby yield Compound 25 in an amount of 0.85 g (66%).

후처리

  1. temperatureby refluxing for three hours
  2. temperaturerefluxed for 24 hours
  3. temperaturecooled to room temperature
  4. customat 0° C.
  5. stirringby stirring for 15 minutes at room temperature
  6. customInsoluble materials were separated through filtration by use of Celite
  7. customthe organic layer was separated from the filtrate
  8. extractionAfter an aqueous layer was extracted with chloroform once
  9. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  10. dry with materialdried over anhydrous sodium sulfate
  11. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-d1d8deba24fc4bfabe0b449243a2abc6
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06403568B1

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