HuagongsheHuagongshe Chemistry Print Report · For research reference only
Succinic anhydride → 1-[2-[(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl] butanedioate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Succinic anhydride | HCID 7922 | — |
| Reactant | Acyclovir | HCID 135398513 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | 1-[2-[(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl] butanedioate | HCID 136096012 | 44% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04146715 |
| Source dataset | uspto-grants-1979_03 |
| ORD ID | ord-d3433ea4e8294ac8acc1fd557776c7f0 |
| Source note | uspto-grants-1979_03 |