HCID 10995419, compound → HCID 453631, compound

HRID 352000Notes

Reaction equation

HRID 352000 reaction equation
COC1C=CC(C([O:22][C@@H:23]2[C:27]([CH2:30][OH:31])([CH2:28][OH:29])[O:26][C@@H:25]([N:32]3[CH:40]=[C:38]([CH3:39])[C:36](=[O:37])[NH:35][C:33]3=[O:34])[CH2:24]2)(C2C=CC=CC=2)C2C=CC(OC)=CC=2)=CC=1>C(O)(=O)C.O>[OH:29][CH2:28][C:27]1([CH2:30][OH:31])[O:26][C@@H:25]([N:32]2[CH:40]=[C:38]([CH3:39])[C:36](=[O:37])[NH:35][C:33]2=[O:34])[CH2:24][C@@H:23]1[OH:22]

Participants

4

Reactant 1

HCID 10995419HCID 10995419, compound

Product 1

HCID 453631HCID 453631, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 3′-O-(4,4′-dimethoxytrityl)-4′-C-hydroxymethylthymidine (6.32 g, 11.0 mmol) in 80% acetic acid in water (50 ml) stood at room temperature for 4 h. Solvents were removed under reduced pressure and water (200 ml) added. The resulting cloudy mixture was washed with ether (3×80 ml) and water was evaporated. The residue was dissolved in methanol and toluene and the resulting solution was concentrated. This process was repeated twice. 4′-C-hydroxymethylthymidine (2.72 g, 91%) was obtained as a foam.

Workup

  1. customSolvents were removed under reduced pressure and water (200 ml)
  2. additionadded
  3. washThe resulting cloudy mixture was washed with ether (3×80 ml) and water
  4. customwas evaporated
  5. dissolutionThe residue was dissolved in methanol
  6. concentrationtoluene and the resulting solution was concentrated

Sources & evidence

ORD record
ord-84e7486b79274501a85e500fd884485a
Source dataset
uspto-grants-2004_06
Patent number
US06743902B1

Reaction notes

Loading…