HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → Artelinate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Npc182939 | HCID 456410 | — |
| Reactant | 1-tert-Butyl-3-ethylcarbodiimide | HCID 4594009 | — |
| Reactant | 4-[[(1R,4R,5S,8S,9S,10R,12R,13S)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]benzoic acid | HCID 71719035 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Artelinate | HCID 73156 | — |
Reaction Steps
Attempts to prepare an hydrazide derivative of artesunate were unsuccessful and resulted in the formation of dihydroartemisinin due to the cyclization reaction. Artelinate was synthesized from dihydroartemisinin as previously described (Shrimali et al. (1998) Indian J. Chem. 37B:1161-1163). Artelinic acid (0.1 g, 0.24 mmol) was dissolved in anhydrous acetonitrile (0.48 mL). To this solution, 1-hydroxybenztriazole (HOBt) (0.038 g, 0.29 mmol) was added, followed by addition of ethyl dimethylethylcarbodiimide (0.055 g, 0.29 mmol). The reaction mixture was stirred at room temperature and monitored by thin-layer chromatography (TLC) until all the acid was converted to the HOBt ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08048850B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-c3defc15bea949658fc4a5ffc314abb0 |
| Source note | uspto-grants-2011_11 |