Sodium Acetate → Ganciclovir Impurity 42

HRID 1285210Notes

Reaction equation

HRID 1285210 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:11][CH2:12]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O-:26])(=[O:25])[CH3:24].[Na+]>CN(C)C=O>[C:23]([O:26][CH2:12][O:11][CH:10]([CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 111630061,3-Dibenzyloxy-2-chloromethoxypropane

Product 1

HCID 11035330Ganciclovir Impurity 42

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
21 °C

Procedure

To a solution of 1,3-di-O-benzyl-2-O-chloromethylglycerol from Preparation II (17.5 g, 55 mmol) in 400 ml of dimethlyformamide at 0° C. under a drying tube was added sodium acetate (6 g). The solution was then warmed to 21° C. and magnetically stirred for 15 hours. The solvent was removed by evaporation at reduced pressure and the oily residue dissolved in 1 pound of diethylether. The ether solution was washed once with 750 ml of water, two times with 250 ml of water, and once with 250 ml of brine, dried over sodium sulfate and concentrated to give 19 g of 2-O-acetoxymethyl-1,3-di-O-benzylglycerol as an oil.

Workup

  1. customThe solvent was removed by evaporation at reduced pressure
  2. dissolutionthe oily residue dissolved in 1 pound of diethylether
  3. washThe ether solution was washed once with 750 ml of water, two times with 250 ml of water
  4. dry with materialonce with 250 ml of brine, dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9996f456ae4f418189b91b9e41b79a97
Source dataset
uspto-grants-1986_01
Patent number
US04565868

Reaction notes

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