Trimethylsilyl triflate → HCID 10746734、化合物

HRID 2186324ノート

反応式

HRID 2186324 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

HCID 10746734HCID 10746734、化合物

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-d1d8deba24fc4bfabe0b449243a2abc6
出典データセット
uspto-grants-2002_06
特許番号
US06403568B1

反応ノート

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