Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | 4-Methylmorpholine | HCID 7972 | — |
| Edukt | 2-Dimethylaminopyridine | HCID 21885 | — |
| Edukt | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Edukt | N-Boc-L-Leucine Hydrate | HCID 12373896 | — |
| Edukt | methyl (5R)-5-((trimethylsilyl)ethynyl)-L-prolinate | HCID 16090847 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | HCID 66757129 | HCID 66757129 | — |
Reaktionsschritte
To a solution of methyl(5R)-5-((trimethylsilyl)ethynyl)-L-prolinate (1.6 grams, 7.48 mmol), dimethylaminopyridine (913 mg, 7.48 mmol), N-methylmorpholine (1.23 mL, 11.22 mmol), and N-(tert-butoxycabonyl)-L-leucine monohydrate (2.24 g, 8.98 mmol) in dichloromethane (30 mL) at room temperature was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.72 g, 8.98 mmol). The resulting mixture was stirred 16 hours at room temperature, and partitioned between ethyl acetate (200 mL) and 1 M HCl (200 mL). The aqueous layer was further extracted with ethyl acetate (200 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated. The residue was chromatographed with a Biotage 40 M cartridge with 40% ethyl acetate/hexane provide the titled compound. MS (DCI/NH3) m/e 439 (M+H)+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patentnummer | US07262207B2 |
|---|
| Quelldatensatz | uspto-grants-2007_08 |
|---|
| ORD ID | ord-6475dbf23a18412185308c156edc9426 |
|---|
| Quellennotiz | uspto-grants-2007_08 |
|---|