Reacción #4262

ord-a74d48ae4860473095f955cf805e25c4

Ecuación de reacción

Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O
Thymidine
CCN(CC)C(F)(F)C(F)Cl
N-(2-chloro-1,1,2-trifluoroethyl)diethylamine
CCO
ethanol
→
Cc1cn2c(nc1=O)O[C@H]1C[C@H]2O[C@@H]1CO
2,3'-anhydrothymidine
Rendimiento 60.3%

Reactantes

Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O
Thymidine
CCN(CC)C(F)(F)C(F)Cl
N-(2-chloro-1,1,2-trifluoroethyl)diethylamine
CCO
ethanol

Reactivos

Ninguno

Disolventes

CN(C)C=O
DMF

Condiciones de reacción

Temperatura
70°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroprepared
  2. 2
    OtroThe product precipitated from this solution
  3. 3
    Filtraciónwas filtered
  4. 4
    FiltraciónThe ethanol supernatant was refrigerated then filtered

Procedimiento

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)diethylamine (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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04724232uspto-grants-1988_02