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

HRID 745654ノート

反応式

HRID 745654 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-70f1e4c2e2dc4667856f7ab4dc73b3d5
出典データセット
uspto-grants-1986_07
特許番号
US04599404

反応ノート

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