Ganciclovir → Ganciclovir Di-O-acetate

HRID 64671

Reaction equation

HRID 64671 reaction equation
[OH:1][CH2:2][CH:3]([O:6][CH2:7][N:8]1[CH:16]=[N:15][C:14]2[C:13](=[O:17])[NH:12][C:11]([NH2:18])=[N:10][C:9]1=2)[CH2:4][OH:5]>CN(C)C1C=CN=CC=1.C(OC(=O)C)(=O)C>[C:2]([O:1][CH2:2][CH:3]([O:6][CH2:7][N:8]1[CH:16]=[N:15][C:14]2[C:13](=[O:17])[NH:12][C:11]([NH2:18])=[N:10][C:9]1=2)[CH2:4][O:5][C:13](=[O:17])[CH3:14])(=[O:1])[CH3:3]

Participants

4

Reactant 1

HCID 135398740Ganciclovir

Product 1

HCID 135459822Ganciclovir Di-O-acetateYield 181.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 3.00 g of 9-(1,3-dihydroxy-2-propoxymethyl)guanine, 300 mg of 4-dimethylaminopyridine, and 100 ml of acetic anhydride was vigorously stirred for 3 days at room temperature. The acetic anhydride was removed by evaporation at reduced pressure and the residue recrystallized from methanol to give 3.62 g of 9-(1,3-diacetyloxy-2-propoxymethyl)guanine, m.p. 237°-239° C.

Workup

  1. customThe acetic anhydride was removed by evaporation at reduced pressure
  2. customthe residue recrystallized from methanol

Sources & evidence

ORD record
ord-ecab7526a4804b5087d56676e3c0b192
Source dataset
uspto-grants-1986_09
Patent number
US04609661

Linked notes

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