HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Hydroxide → Stavudine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 72016-54-7 | HCID 126354 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | HCID 70036919 | HCID 70036919 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | Stavudine | HCID 18283 | 79% |
Reaction Steps
In this synthesis, dimesylthymidine 1 was first treated with sodium hydroxide (3 equivalents) in refluxing water for 2 hours and after work-up the resultant 3,5-anhydrothymidine was treated with potassium t-butoxide in dimethylsulfoxide (DMSO) at room temperature for 2 hours. The reaction mixture was neutralized, evaporated to dryness and after a series of manipulations which included extraction, decolourization, precipitation and recrystallization, gave Stavudine in 79% yield and an overall yield of 56%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06635753B1 |
| Source dataset | uspto-grants-2003_10 |
| ORD ID | ord-182aaade9989458b89f633f523d3aa88 |
| Source note | uspto-grants-2003_10 |