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Pyridine → HCID 70171875, 화합물

HRID 2229753
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HRID 2229753 반응식
[C:1]([NH:4][C:5]1[CH:19]=[CH:18][N:8]([C@@H:9]2[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[C@H:10]2[F:17])[C:7](=[O:20])[N:6]=1)(=[O:3])[CH3:2].N1C=CC=CC=1.[CH3:27][O:28][C:29]1[C:30]([O:49][CH3:50])=[C:31]([CH:46]=[CH:47][CH:48]=1)[C:32](Cl)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C)C1C=CN=CC=1.CO>[CH3:27][O:28][C:29]1[C:30]([O:49][CH3:50])=[C:31]([CH:46]=[CH:47][CH:48]=1)[C:32]([O:15][CH2:14][C@H:13]1[O:16][C@@H:9]([N:8]2[CH:18]=[CH:19][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:6][C:7]2=[O:20])[C@H:10]([F:17])[C@@H:11]1[OH:12])([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 1049PyridineHCID 22094552N-Acetyl-2'-deoxy-2'-fluorocytidineHCID 66624882Dimethoxytrityl chloride

생성물 1

HCID 70171875HCID 70171875, 화합물

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 887Methanol용매

실험 절차

4 mmol of 4-N-acetyl-2′-fluoro-2′-deoxycytidine are taken up in 25 ml of abs. pyridine in a 100 ml Schlenk flask and, at room temperature, 1.3 g (about 4.4 mmol) of dimethoxytrityl chloride and 20 mg of 4-dimethylaminopyridine are added. After three hours, 1 ml of methanol was added to the mixture, which was then evaporated to dryness in vacuo. The remaining oil is taken up in 50 ml of methylene chloride (deacidified over aluminum oxide) and extracted three times with 50 ml of water. The organic phase is dried over sodium sulfate. After the methylene chloride had been stripped off, the crude product remained as solid foam. The crude product is purified by chromatography on silica gel 60H (column 2×20 cm, mobile phase methylene chloride with 0.1% pyridine, gradient methanol). The product was eluted with 3% methanol in methylene chloride. After the solvent has been stripped off, 1.39 g (59% of theory) of a white foamy solid remain.

후처리

  1. customwas then evaporated to dryness in vacuo
  2. extractionextracted three times with 50 ml of water
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customThe crude product is purified by chromatography on silica gel 60H (column 2×20 cm, mobile phase methylene chloride with 0.1% pyridine, gradient methanol)
  5. washThe product was eluted with 3% methanol in methylene chloride

출처 및 근거

ORD 기록
ord-19559ed652ea4cafbd131193eceb8dcb
출처 데이터셋
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06420546B1

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