Succinic anhydride → HCID 178508934, compound

HRID 2209399Notes

Reaction equation

HRID 2209399 reaction equation
[CH:1]1[N:5]([CH2:6][O:7][CH2:8][CH2:9][OH:10])[C:4]2[N:11]=[C:12]([NH2:16])[N:13]=[C:14]([OH:15])[C:3]=2[N:2]=1.[C:17]1(=[O:23])[O:22][C:20](=[O:21])[CH2:19][CH2:18]1.C(N(CC)CC)C>CN(C)C=O>[CH:1]1[N:5]([CH2:6][O:7][CH2:8][CH2:9][OH:10])[C:4]2[N:11]=[C:12]([NH2:16])[N:13]=[C:14]([OH:15])[C:3]=2[N:2]=1.[C:17]([O-:22])(=[O:23])[CH2:18][CH2:19][C:20]([O-:7])=[O:21]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 178508933HCID 178508933, compound

Product 1

HCID 178508934HCID 178508934, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Acyclovir succinate is prepared by heating a solution of 0.2252 g of acyclovir (1 mmol) (Sigma), 0.200 g of succinic anhydride (2 mmoles) (Aldrich) and 0.14 mL of triethylamine in 15 mL of dry dimethylformamide at 60° C. in an oil bath for 21 hours. The solution was then cooled and the volatile constituents were evaporated in vacuo, and the residue was taken up in 8 mL of ice water and acidified to pH 2 with 2N HCl. A white precipitate was formed that was collected by filtration, thoroughly washed with ice water and dried in vacuo over P2O5 at 40° C. to yield 0.180 g (54 percent) of the product. The ester was then recrystallized from methanol and characterized by IR and 1H NMR spectroscopy.

Workup

  1. temperatureThe solution was then cooled
  2. customthe volatile constituents were evaporated in vacuo
  3. customA white precipitate was formed
  4. filtrationthat was collected by filtration
  5. washthoroughly washed with ice water
  6. dry with materialdried in vacuo over P2O5 at 40° C.

Sources & evidence

ORD record
ord-a9ed80aa2cf441b5a65ca557eaf92350
Source dataset
uspto-grants-1995_10
Patent number
US05455027

Reaction notes

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