Triethylamine → 2'-deoxy-3',5'-di-O-acetyl-3-(2,3-dimethoxybenzoyl)-5-fluorouridine

HRID 745654노트

반응식

HRID 745654 반응식
[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[O:8][C@@H:7]([N:15]2[CH:22]=[C:21]([F:23])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH2:6]1)(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:31][O:32][C:33]1[C:41]([O:42][CH3:43])=[CH:40][CH:39]=[CH:38][C:34]=1[C:35](Cl)=[O:36]>O1CCOCC1>[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[O:8][C@@H:7]([N:15]2[CH:22]=[C:21]([F:23])[C:19](=[O:20])[N:18]([C:35](=[O:36])[C:34]3[CH:38]=[CH:39][CH:40]=[C:41]([O:42][CH3:43])[C:33]=3[O:32][CH3:31])[C:16]2=[O:17])[CH2:6]1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 27583922,3-Dimethoxybenzoyl chlorideHCID 127901643',5'-Di-O-acetyl-2'-deoxy-5-fluorouridine

생성물 1

HCID 131898982'-deoxy-3',5'-di-O-acetyl-3-(2,3-dimethoxybenzoyl)-5-fluorouridine수율 88.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

15.0 g of 2'-deoxy-3',5'-di-O-acetyl-5-fluorouridine and 15 ml of triethylamine were dissolved in 75 ml of dry dioxane, and the resulting solution was cooled with ice. To the solution was added 13.6 g of 2,3-dimethoxybenzoyl chloride, and the resulting mixture was allowed to stand at room temperature for 30 minutes and then at 90° C. for 30 minutes. The crystals produced were filtered off, and the filtrate was concentrated under reduced pressure. To the oily residue was added 200 ml of ethanol. Upon heating, the mixture began to separate crystals while the oily residue was dissolved. After dissolving the oily residue completely, the mixture was cooled, and there was obtained 2'-deoxy-3',5'-di-O-acetyl-3-(2,3-dimethoxybenzoyl)-5-fluorouridine as crystals. Recrystallization of the product from ethanol afforded 19.65 g (yield: 88.4%) or colorless needles having a melting point of 139 to 141° C. The structure was supported by the absorption spectra and elemental analysis.

후처리

  1. temperaturethe resulting solution was cooled with ice
  2. waitat 90° C. for 30 minutes
  3. customThe crystals produced
  4. filtrationwere filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionTo the oily residue was added 200 ml of ethanol
  7. temperatureUpon heating
  8. customto separate crystals while the oily residue
  9. dissolutionwas dissolved
  10. dissolutionAfter dissolving the oily residue completely
  11. temperaturethe mixture was cooled

출처 및 근거

ORD 기록
ord-70f1e4c2e2dc4667856f7ab4dc73b3d5
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04599404

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