Sodium Bicarbonate → HCID 18650250, compound

HRID 1613138Notes

Reaction equation

HRID 1613138 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@:13]([CH:16]=[N:17]O)([CH2:14][OH:15])[O:12][C@@H:11]([N:19]2[CH:27]=[C:25]([CH3:26])[C:23](=[O:24])[NH:22][C:20]2=[O:21])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:28][C:29]([O-])=[O:30].[Na+].C([O-])(O)=O.[Na+]>CC(OC(C)=O)=O>[Si:1]([O:8][C@@H:9]1[C@@:13]([C:16]#[N:17])([CH2:14][O:15][C:29](=[O:30])[CH3:28])[O:12][C@@H:11]([N:19]2[CH:27]=[C:25]([CH3:26])[C:23](=[O:24])[NH:22][C:20]2=[O:21])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 88479245HCID 88479245, compound

Product 1

HCID 18650250HCID 18650250, compoundYield 4,703.9%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3'-O-t-butyldimethylsilyl-4'-hydroxyiminomethylthymidine (1.98 g, 4.95 mM) the compounds of Formula 13, prepared, e.g., as described in Preparation 9) with NaOAc (7 mg, 0.09 mM) in Ac2O (7 ml) was stirred at 80° C. for 72 hours, allow to cool and treated with 10 g of ice followed by sat. NaHCO3. The solution was extracted CH2Cl2 (3×100 ml), and the organic phases were combined and dried over Na2SO4. The solvent was removed by evaporation and the residue was purified by flash column chromatography silica gel eluting with (20% acetone/CH2Cl2) affording 3'-O-t-butyldimethylsilyl-4'-cyano-5'-O-acetylthymidine (1.7 g, 4.0 mM). MP 67°-69° C.

Workup

  1. temperatureto cool
  2. extractionThe solution was extracted CH2Cl2 (3×100 ml)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed by evaporation
  5. customthe residue was purified by flash column chromatography silica gel eluting with (20% acetone/CH2Cl2)

Sources & evidence

ORD record
ord-8287c2955fd044a59e85b1669c6393cb
Source dataset
uspto-grants-1993_03
Patent number
US05192749

Reaction notes

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