Ethanol → 2,3'-Anhydrothymidine

HRID 1885525Notes

Reaction equation

HRID 1885525 reaction equation
[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.ClC(F)C(N(CC)CC)(F)F.C(O)C>CN(C=O)C>[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

Participants

5

Reactant 3

HCID 702EthanolHCID 5789ThymidineHCID 1361842-Chloro-N,N-diethyl-1,1,2-trifluoroethan-1-amine

Product 1

HCID 69157522,3'-Anhydrothymidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Thymidine (85.4 g: 0.353 mol) was dissolved in 500 ml dry DMF 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 them poured into 950 ml ethanol (EtOH) with vigorous stirring. The product precipitated from this solution was filtered. The EtOH supernatent was refrigerated then filtered to yield a total of 47.75 g (0.213 mol. 60.3%) mp=228°-230° c.

Workup

  1. customprepared
  2. customThe product precipitated from this solution
  3. filtrationwas filtered
  4. filtrationThe EtOH supernatent was refrigerated then filtered
  5. customto yield a total of 47.75 g (0.213 mol. 60.3%) mp=228°-230° c

Sources & evidence

ORD record
ord-f610bcba676a46c28c9947766a7a4977
Source dataset
uspto-grants-1992_09
Patent number
US05145840

Reaction notes

Loading…