HCID 18650248, compound → HCID 453662, compound

HRID 1613144Notes

Reaction equation

HRID 1613144 reaction equation
[C:1]([C@:3]1([CH2:17][O:18]C(=O)C)[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][CH2:4]1)#[N:2]>[NH4+].[OH-]>[C:1]([C@:3]1([CH2:17][OH:18])[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][CH2:4]1)#[N:2]

Participants

3

Reactant 1

HCID 18650248HCID 18650248, compound2×

Product 1

HCID 453662HCID 453662, compound

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
24 °C

Procedure

The 4'-α and 4'-β isomers of 3'-deoxy-4'-cyano-5'-O-acetylthymidine (Formula 30) (26 mg, 0.09 mM) is dissolved in 0.2 ml NH4OH/0.2 ml CH3OH and stirred at 24° C. for 2 hours. The solvent is removed by evaporation and the residue chromatographed on silica gel (Preparative TLC, 2 plates, 1000 microns) using 1% CH3OH/EtOAc with 0.8% NH4OH, affording the 4'-α and 4'-β isomers of 3'-deoxy-4'-cyanothymidine, 6 mg, 0.024 mM, MS 251 (M+); and 11 mg, 0.044 mM, MS 251(M+), respectively.

Workup

  1. customThe solvent is removed by evaporation
  2. customthe residue chromatographed on silica gel (Preparative TLC, 2 plates, 1000 microns)

Sources & evidence

ORD record
ord-64c7c32a36ff43059b86eff6316cbf48
Source dataset
uspto-grants-1993_03
Patent number
US05192749

Reaction notes

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