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

HRID 1818671

반응식

HRID 1818671 반응식
[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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-75d7d11728584fe4b4c7a4009ae12309
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601702B2

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