Borane → 2'-o-Phthalimidoethyl-5-methyluridine

HRID 1358087

Reaktionsgleichung

Reaktionsgleichung von HRID 1358087
[OH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].B.[H][H].[CH3:18][C:19]1[C:33](=[O:34])[N:32]=[C:31]2[N:21]([C@@H:22]3[O:26][C@H:25]([CH2:27][OH:28])[C@@H:24]([OH:29])[C@@H:23]3[O:30]2)[CH:20]=1.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C.CO>[C:8]1(=[O:9])[N:4]([CH2:3][CH2:2][O:1][C@@H:23]2[C@H:24]([OH:29])[C@@H:25]([CH2:27][OH:28])[O:26][C@H:22]2[N:21]2[CH:20]=[C:19]([CH3:18])[C:33](=[O:34])[NH:32][C:31]2=[O:30])[C:5](=[O:14])[C:6]2=[CH:13][CH:12]=[CH:11][CH:10]=[C:7]12

Komponenten

8

Edukt 5

HCID 6331BoraneHCID 77499N-(2-Hydroxyethyl)phthalimideHCID 1680452,2'-Anhydro-1-beta-arabinofuranosylthymineHCID 516892Sodium BicarbonateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 100028392'-o-Phthalimidoethyl-5-methyluridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 21584119Ethylacetate methanolLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

N-(2-Hydroxyethyl)phthalimide (277 g, 1.45 mol) was slowly added to a solution of borane in tetrahydrofuran (1 M, 600 mL), with stirring. Hydrogen gas evolved as the solid dissolved. Once the rate of gas evolution subsided, the solution was placed in a 2 L stainless steel bomb. 2,2′-Anhydro-5-methyluridine (60 g, 0.25 mol) and sodium bicarbonate (120 mg) were added and the bomb was sealed. After 30 minutes, the bomb was vented and placed in an oil bath and heated to 150° C. internal temperature for 24 h. The bomb was cooled to room temperature and opened. TLC (ethyl acetate-methanol; 95:5) revealed the disappearance of starting material. The crude solution was concentrated and the residue was purified by chromatography on silica gel starting with ethyl acetate to remove the excess phthalimide reagent, followed by ethyl acetate-methanol (95:5) to elute 2 (22.2 g, 20.6%).

Aufarbeitung

  1. dissolutiondissolved
  2. customthe bomb was sealed
  3. customplaced in an oil bath
  4. temperatureThe bomb was cooled to room temperature
  5. concentrationThe crude solution was concentrated
  6. customthe residue was purified by chromatography on silica gel starting with ethyl acetate
  7. customto remove the excess phthalimide reagent
  8. washto elute 2 (22.2 g, 20.6%)

Quellen und Nachweise

ORD-Eintrag
ord-2314e7c75e404e09a27522b06028cd6b
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593466B1

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