HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → Tenofovir
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 9-(2-Hydroxypropyl)adenine, (R)- | HCID 445211 | — |
| Reactant | Diethyl P-[[[(4-methylphenyl)sulfonyl]oxy]methyl]phosphonate | HCID 4193599 | — |
| Reactant | Magnesium 2-methylpropan-2-olate | HCID 12040442 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Tenofovir | HCID 464205 | — |
Reaction Steps
Accordingly (R)-9-[2-(hydroxyl)propyl]adenine is condensed with Diethyl p-toluene sulfonyloxy methylphosphonate in presence of Magnesium tert-butoxide in a polar solvent preferably dimethylformamide at a temperature of 70° C. to 80° C. After the reaction completion the reaction mass is neutralized by adding an acid preferably acetic acid and the solvent is distilled off completely. The obtained crude is dissolved in a chlorinated hydrocarbon selected from Methylenedichloride, chloroform, and Ethylene dichloride and water is added. The reaction mixture is filtered to remove the salts and Methylenedichloride layer is separated. Methylenedichloride is distilled off completely to get (R)-9-[2-(phosphonomethoxy)propyl]adenine.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08049009B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-1c01f1b6a05443549967b3ba56551380 |
| Source note | uspto-grants-2011_11 |