Isophthaloyl chloride → HCID 178476350, 화합물

HRID 703549노트

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HRID 703549 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.[OH:47][C:48]1[CH:53]=[CH:52][NH:51][C:50](=[O:54])[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:47][C:48]4[CH:53]=[CH:52][N:51]=[C:50]([OH:54])[CH:49]=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 물질

6

반응물 4

HCID 7451Isophthaloyl chlorideHCID 8471Triethylamine2회HCID 136874845'-O-acetyl-3'-O-benzyl-2'-deoxy-5-fluorouridineHCID 546960044-Hydroxy-2(1H)-pyridinone

생성물 1

HCID 178476350HCID 178476350, 화합물수율 30.1%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

To a solution of 3.00 g of 5'-O-acetyl-3'--O--benzyl- 2'-deoxy-5-fluorouridine in 100 ml of dry dioxane were added 2.40 g of isophthaloyl chloride and 8.5 ml of triethylamine, and the mixture was refluxed for 2 hours. Then, to the reaction mixture were added a suspension of 1.77 g of 4-hydroxy-2(1H)-pyridone and 9.60 ml of triethylamine in 100 ml of dry dioxane, and the mixture was refluxed for 2 hours. The insolubles were removed by filtration and the filtrate was concentrated. The residue was dissolved in 100 ml of ethyl acetate, and the solution was washed twice with 30 ml of saturated aqueous solution of sodium chloride. The ethyl acetate layer was dried on anhydrous sodium, sulfate and concentrated. The residue was placed on a silica gel column to conduct a gradient elution using chloroform and mixtures of methanol (up to 2%) and chloroform. The fractions corresponding to the title compound were collected and concentrated to dryness, giving 1.48 g of the title compound as a powder in a yield of 30%.

후처리

  1. temperaturethe mixture was refluxed for 2 hours
  2. additionThen, to the reaction mixture were added
  3. temperaturethe mixture was refluxed for 2 hours
  4. customThe insolubles were removed by filtration
  5. concentrationthe filtrate was concentrated
  6. dissolutionThe residue was dissolved in 100 ml of ethyl acetate
  7. washthe solution was washed twice with 30 ml of saturated aqueous solution of sodium chloride
  8. dry with materialThe ethyl acetate layer was dried on anhydrous sodium, sulfate
  9. concentrationconcentrated
  10. washa gradient elution
  11. customThe fractions corresponding to the title compound were collected
  12. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-4b1fbd5698854f948801056f0d61c61f
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04983609

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