HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilyl iodide → (S)-N-(2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilyl iodide | HCID 85247 | — |
| Reactant | Apremilast | HCID 11561674 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | (S)-N-(2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide | HCID 68088610 | — |
Reaction Steps
To a stirred solution of (S)—N-{2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide (1 mmol) in anhydrous CH2Cl2, is added iodotrimethylsilane (6 mmol). The mixture is stirred at room temperature for 24 hours. The reaction mixture is diluted with brine and is extracted with CH2Cl2. The CH2Cl2 is removed to give crude (S)—N-{-2-[1-(3-ethoxy-4-hydroxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide. The product is purified by recrystallization.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08853175B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-595bd32be902425597cbf3e4eee634d6 |
| Source note | uspto-grants-2014_10 |