Ethanol → 2,3'-Anhydrothymidine

HRID 620003

Reaktionsgleichung

Reaktionsgleichung von HRID 620003
[C@@H:1]1([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3](O)[CH2:2]1.C(O)C>CN(C)C=O>[CH3:16][C:15]1[C:13](=[O:14])[N:12]=[C:10]2[N:9]([C@@H:1]3[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([O:11]2)[CH2:2]3)[CH:17]=1

Komponenten

4

Edukt 2

HCID 702EthanolHCID 5789Thymidine

Produkt 1

HCID 69157522,3'-AnhydrothymidineAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Thymidine (85.4 g; 0.353 mol) was dissolved in 500 mL dry DMF (dimethyl formamide) and added to N-(2-chloro-1,1,2-trifluoroethyl)dielthylamine (100.3 g; 0.529 mol) [prepared according to the method of D. E. Ayer, J. Med. Chem. 6, 608 (1963)]. This solution was heated at 70° C. for 30 minutes then poured into 950 mL ethanol with vigorous stirring. The product precipitated from this solution and was filtered. The ethanol supernatant was refrigerated then filtered to yield a total of 47.75 g (0.213 mol; 60.3%) of 2,3'-anhydrothymidine mp=228°-230° C.

Aufarbeitung

  1. additionadded to N-(2-chloro-1,1,2-trifluoroethyl)dielthylamine (100.3 g; 0.529 mol) [
  2. customprepared
  3. customThe product precipitated from this solution
  4. filtrationwas filtered
  5. filtrationThe ethanol supernatant was refrigerated then filtered

Quellen und Nachweise

ORD-Eintrag
ord-85d2378aa653482c92bb7fea59933355
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04818750

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