Uridine, 3'-azido-2',3'-dideoxy-5'-O-(triphenylmethyl)- → 3'-Amino-5'-O-trityl-2',3'-dideoxyuridine

HRID 1818671

反応式

HRID 1818671 の反応式
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][O:10][C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:7][C@@H:6]([N:30]2[CH:37]=[CH:36][C:34](=[O:35])[NH:33][C:31]2=[O:32])[CH2:5]1)=[N+]=[N-]>C(O)C>[NH2:1][C@@H:4]1[C@@H:8]([CH2:9][O:10][C:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:7][C@@H:6]([N:30]2[CH:37]=[CH:36][C:34](=[O:35])[NH:33][C:31]2=[O:32])[CH2:5]1

参加物

3

反応物 1

HCID 13711964Uridine, 3'-azido-2',3'-dideoxy-5'-O-(triphenylmethyl)-

生成物 1

HCID 529147963'-Amino-5'-O-trityl-2',3'-dideoxyuridine収率 70%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Lidlar's catalyst (20 mg) was added to compound 30 (0.10 g, 0.20 mmol), and was then suspended in ethanol (5 ml). Air was removed from the flask by flushing with nitrogen several times. The nitrogen was then removed and replaced with hydrogen. The mixture was stirred for 5 hours, and then filtered through Celite. Fresh Lidlar's catalyst (20 mg) was added to the filtrate. The flask was flushed with nitrogen and then hydrogen as previously, and the reaction was left stirring for another 3 hours. The reaction mixture was filtered through Celite. The solvent was evaporated and the concentrated solution was purified by column chromatography (MeOH/DCM 2%→10%) which gave the title product as a white solid (0.065 g, 70%). Rf: 0.3 in DCM/MeOH 90:10.

後処理

  1. customAir was removed from the flask
  2. customby flushing with nitrogen several times
  3. customThe nitrogen was then removed
  4. filtrationfiltered through Celite
  5. additionFresh Lidlar's catalyst (20 mg) was added to the filtrate
  6. customThe flask was flushed with nitrogen
  7. waithydrogen as previously, and the reaction was left
  8. stirringstirring for another 3 hours
  9. filtrationThe reaction mixture was filtered through Celite
  10. customThe solvent was evaporated
  11. customthe concentrated solution was purified by column chromatography (MeOH/DCM 2%→10%) which

出典と根拠

ORDレコード
ord-75d7d11728584fe4b4c7a4009ae12309
出典データセット
uspto-grants-2009_10
特許番号
US07601702B2

関連ノート

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