Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 90224866 | HCID 90224866 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 90224810 | HCID 90224810 | 92.2% |
Reaction Steps
To a solution of (E)-1-(4-(2-(1,4-dioxa-8-azaspiro[4.5]decan-8-ylsulfonyl)vinyl)-3,5-dimethylphenyl)-5,5-dimeth ylimidazolidine-2,4-dione (1.2 g, 2.58 mmol) in tetrahydrofuran (26 mL), a 2 N aqueous hydrochloric acid solution (26 mL, 52 mmol) was added dropwise over ten minutes. The mixture was stirred at 60° C. for two hours. The reaction mixture was cooled, followed by adjustment of its pH to 7 using a 2 N aqueous sodium hydroxide solution, and this mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate) to afford (E)-1-(3,5-dimethyl-4-(2-((4-oxopiperidin-1-yl)sulfonyl)vinyl)phenyl)-5,5-dimethylimidazolidine-2,4-dione (998 mg, 92%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09428505B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-77af8969286b446c91bc2e40fdf0a462 |
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| Source note | uspto-grants-2016_08 |
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