Succinic anhydride → 1-[2-[(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl] butanedioate

HRID 848094Notes

Reaction equation

HRID 848094 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2.[C:17]1(=[O:23])[O:22][C:20](=[O:21])[CH2:19][CH2:18]1>N1C=CC=CC=1>[C:20]([CH2:19][CH2:18][C:17]([O:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2)=[O:23])([OH:22])=[O:21]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 135398513Acyclovir

Product 1

HCID 1360960121-[2-[(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl] butanedioateYield 44%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 9-(2-hydroxyethoxymethyl)guanine (0.25 g), succinic anhydride (0.55 g) and pyridine (50 ml) was heated under anhydrous conditions on a steam bath overnight. The solvent was evaporated under reduced pressure at ∠40° C., the last trace being removed azeotropically with toluene. The residue was triturated with acetone and the product removed by filtration. Recrystallization from methanol afforded 9-{2-(3-carboxypropionyloxy)ethoxymethyl}guanine, m.p. 203°-207° C. (sinter 190° C.), in 44% yield.

Workup

  1. temperaturewas heated under anhydrous conditions on a steam bath overnight
  2. customThe solvent was evaporated under reduced pressure at ∠40° C.
  3. customthe last trace being removed azeotropically with toluene
  4. customThe residue was triturated with acetone
  5. customthe product removed by filtration
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-995dabbb899d4676b65cd66a9465f548
Source dataset
uspto-grants-1981_10
Patent number
US04294831

Reaction notes

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