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Isophthaloyl chloride → 5'-O-acetyl-3-[3-(4-benzoyloxy-5-chloro-2-pyridyloxycarbonyl)benzoyl]-3'-O-benzyl-2'-deoxy-5-fluorouridine

HRID 1607328
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HRID 1607328 반응식
[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:18]=[C:17]([F:19])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:8][C@@H:7]1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:3])[CH3:2].[C:28](Cl)(=[O:38])[C:29]1[CH:37]=[CH:36][CH:35]=[C:31]([C:32](Cl)=[O:33])[CH:30]=1.C(N(CC)CC)C.[C:47]([O:55][C:56]1[C:61]([Cl:62])=[CH:60][NH:59][C:58](=[O:63])[CH:57]=1)(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>O1CCOCC1>[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:18]=[C:17]([F:19])[C:15](=[O:16])[N:14]([C:28](=[O:38])[C:29]3[CH:37]=[CH:36][CH:35]=[C:31]([C:32]([O:63][C:58]4[CH:57]=[C:56]([O:55][C:47](=[O:54])[C:48]5[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=5)[C:61]([Cl:62])=[CH:60][N:59]=4)=[O:33])[CH:30]=3)[C:12]2=[O:13])[CH2:8][C@@H:7]1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 7451Isophthaloyl chlorideHCID 8471Triethylamine2회HCID 136874845'-O-acetyl-3'-O-benzyl-2'-deoxy-5-fluorouridineHCID 140496465-Chloro-2-oxo-1,2-dihydropyridin-4-yl benzoate

생성물 1

HCID 186348145'-O-acetyl-3-[3-(4-benzoyloxy-5-chloro-2-pyridyloxycarbonyl)benzoyl]-3'-O-benzyl-2'-deoxy-5-fluorouridine수율 37.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of 0.60 g of 5'-O-acetyl-3'-O-benzyl-2'-deoxy-5-fluorouridine in 30 ml of dry dioxane were added 0.42 g of isophthaloyl chloride and 1.11 ml of triethylamine, and the mixture was refluxed for 2 hours. Then 0.60 g of 4-benzoyloxy-5-chloro-2(1H)-pyridone and 1.11 ml of triethylamine were added and the resulting mixture was refluxed for 1 hour. The precipitate thus formed was filtered off, and the filtrate was concentrated. The residue was placed on a silica gel column and eluted with 40% ethyl acetate-benzene, giving 0.45 g of the title compound in a yield of 37%.

후처리

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperaturethe resulting mixture was refluxed for 1 hour
  3. customThe precipitate thus formed
  4. filtrationwas filtered off
  5. concentrationthe filtrate was concentrated
  6. washeluted with 40% ethyl acetate-benzene

출처 및 근거

ORD 기록
ord-759370d38f634277a705f5c992403832
출처 데이터셋
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04864021

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