HCID 453660, compound → HCID 18650248, compound

HRID 1613141Notes

Reaction equation

HRID 1613141 reaction equation
O[N:2]=[CH:3][C@:4]1([CH2:18][OH:19])[O:8][C@@H:7]([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:6][CH2:5]1.[CH3:20][C:21]([O-])=[O:22].[Na+]>C(OC(=O)C)(=O)C>[C:3]([C@:4]1([CH2:18][O:19][C:21](=[O:22])[CH3:20])[O:8][C@@H:7]([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:6][CH2:5]1)#[N:2]

Participants

4

Reactant 2

HCID 453660HCID 453660, compound2×HCID 517045Sodium Acetate

Product 1

HCID 18650248HCID 18650248, compoundYield 149.2%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the 4'-α and 4'-β isomers of 3'-deoxy-4'-hydroxyiminomethylthymidine (40 mg, 0.15 mM) (Formula 24) in 0.5 ml acetic anhydride, was added NaOAc (6 mg, 0.07 mM) and stir at 100° C. for 24 hours. The solvent was removed by evaporation and the residue chromatographed on silica gel using 4% CH3OH/CH2Cl2, affording the 4'-α and 4'-β isomers of 3'-deoxy-4'-cyano-5'-O-acetylthymidine (32 mg, 0.11 mM).

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue chromatographed on silica gel using 4% CH3OH/CH2Cl2

Sources & evidence

ORD record
ord-6e67a53d24da4fcba5a2398f5d5943c4
Source dataset
uspto-grants-1993_03
Patent number
US05192749

Reaction notes

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