Potassium Cyanide → HCID 86745215, compound

HRID 973798Notes

Reaction equation

HRID 973798 reaction equation
[C:1]([CH:4]([OH:22])[C@H:5]1[O:9][C@@H:8]([N:10]2[CH:17]=[C:16](I)[C:14](=[O:15])[NH:13][C:11]2=[O:12])[CH2:7][C@@H:6]1[N:19]=[N+:20]=[N-:21])(=[O:3])[CH3:2].[C-]#N.[K+].CC([O-])=O.[K+].[N:31]([C@@H:34]1[C@@H](CO)O[C@@H](N2C=C(C)C(=S)NC2=O)C1)=[N+]=[N-]>CS(C)=O>[C:1]([CH:4]([OH:22])[C@H:5]1[O:9][C@@H:8]([N:10]2[CH:17]=[C:16]([C:34]#[N:31])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[CH2:7][C@@H:6]1[N:19]=[N+:20]=[N-:21])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 9032Potassium CyanideHCID 517044Potassium AcetateHCID 30002543'-Azido-3'-deoxy-4-thiothymidineHCID 86745214HCID 86745214, compound

Product 1

HCID 86745215HCID 86745215, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5'-Acetyl-3'-azido-2',3'-dideoxy-5-iodouridine(0.5 g, 1.2 mMol, Ex.) was treated with KCN(0.1 g, 1.6 mMol) and KOAc(0.15 g, 1.6 mMol) in anhydrous DMSO at 105° C. for 90 minutes in a method analogous to (1). The DMSO was evaporated in vacuo and the residue chromatographed on silica gel, eluted with CHCl3 then with 20:1 CHCl3/MeOH (v/v). Collection of appropriate fractions followed by evaporation of the solvents gave pure 5'-acetyl-3'-azido-5-cyano-2',3'-dideoxyuridine. This material was dissolved in NH3 saturated MeOH at ambient temperature and allowed to stand overnight. The solvents were evaporated in vacuo and the residue chromatographed on silica gel using 9:1 CHCl3/MeOH (v/v) as the eluting solvent. Collection and evaporation of the appropriate fractions yielded the title compound as a clear oil: UV(nm): at pH 1 λmax=276,214 (ε=13700,12800), λmin=238 (ε=2200); at pH 13 λmax=275 (ε=10000), λmin=245(ε=3200); H NMR(DMSO-d6) δ8.81(s,1H,H6), 5.95(dd,1H,H1',J=2.34,4.11 Hz), 5.45(t,1H,5'OH,J=5.08 Hz), 4.4-4.3(m,1H,H3'), 3.9-3.8(m,1H,H4'), 3.8-3.5(m,2H,H5'), 2.45-2.30(m,2H,H2').

Workup

  1. customThe DMSO was evaporated in vacuo
  2. customthe residue chromatographed on silica gel
  3. washeluted with CHCl3
  4. customCollection of appropriate fractions
  5. customfollowed by evaporation of the solvents

Sources & evidence

ORD record
ord-9dcb964cb5ed4a299061de14b1734088
Source dataset
uspto-grants-1991_11
Patent number
US05064946

Reaction notes

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