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

HRID 1154527
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1154527
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

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

Produkt 1

HCID 131898982'-deoxy-3',5'-di-O-acetyl-3-(2,3-dimethoxybenzoyl)-5-fluorouridineAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-Dioxane
Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b5f5223d8ccf47089fe9be75c6e7c783
Quelldatensatz
uspto-grants-1984_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04490366

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