Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Hydrogen Peroxide | HCID 784 | — |
| Edukt | Sodium Hydroxide | HCID 14798 | — |
| Edukt | N-(1-cyano-4-(4-ethoxy-3-methylphenylsulfonamido)cyclohexyl)acetamide | HCID 67223797 | — |
| Lösungsmittel | Ethanol | HCID 702 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Produkt | HCID 67224897 | HCID 67224897 | 48,3% |
Reaktionsschritte
5N Sodium hydroxide (320 ul, 1.59 mmol) followed by 50% aqueous hydrogen peroxide (157 ul, 2.55 mmol) were added to solution of N-(1-cyano-4-(4-ethoxy-3-methylphenylsulfonamido)cyclohexyl)acetamide (Intermediate 126, 242 mg, 0.638 mmol) in ethanol (6.4 ml). The reaction was heated to 80° C. for three hours. LCMS indicated approximately 3:1 product:starting material by co-injection. The reaction was diluted with water and extract with four volumes ethyl acetate. The combined organics were dried over sodium sulfate, filtered and concentrate to 226 mg crude. TLC (10% methanol in ethyl acetate): Rf starting material 0.66; major spot Rf=0.25. The crude was chromatographed on Biotage 12M eluting 0-100% ethyl acetate in (10% methanol in ethyl acetate) to give the product as an off-white solid (117 mg, 0.308 mmol). LCMS [M+H]=380.2.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08394858B2 |
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| Quelldatensatz | uspto-grants-2013_03 |
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| ORD ID | ord-1e07e2d0db0a4902aa10cc40ff7066e6 |
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| Quellennotiz | uspto-grants-2013_03 |
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