HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Hydrochloric Acid → Methyl (2S,3S,5S)-3-[(hydroxyamino)carbonyl]-5-([(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyloxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1-carboxylate
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Hydrochloric Acid | HCID 313 | — |
| Edukt | Hydroxylamine | HCID 787 | — |
| Edukt | Hydroxyamine hydrochloride | HCID 443297 | — |
| Edukt | Sodium Methoxide | HCID 10942334 | — |
| Edukt | dimethyl(2S,3S,5S)-5-([(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyloxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate | HCID 67304285 | — |
| Lösungsmittel | Methanol | HCID 887 | — |
| Produkt | Methyl (2S,3S,5S)-3-[(hydroxyamino)carbonyl]-5-([(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyloxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1-carboxylate | HCID 86598252 | 76% |
Reaktionsschritte
To a solution of dimethyl (2S,3S,5S)-5-([(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyloxy)-2-[(4-phenylpiperazin 1-yl)carbonyl]piperidine-1,3-dicarboxylate (66 mg, 0.00012 mol) in methanol (0.57 mL, 0.014 mol) was added 1.640 M of N-hydroxyamine in methanol solution (1.511 mL), made from the hydroxylamine HCl salt and sodium methoxide freshly. The mixture was stirred at rt for 1 h and acidified with 1N HCl. The resulting mixture was applied directly on RP-HPLC to yield the desired compound (61 mg, 76%). MS (ESI): (M+H)+=534.2.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08853243B2 |
| Quelldatensatz | uspto-grants-2014_10 |
| ORD ID | ord-6bc0f5e28c7f44e695714fca425d03c7 |
| Quellennotiz | uspto-grants-2014_10 |