Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Edukt | 2-Chloro-4-fluorobenzylamine | HCID 139909 | — |
| Edukt | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Edukt | (S)-1-Benzyl-5-carboxy-2-pyrrolidinone | HCID 10900113 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | HCID 49864914 | HCID 49864914 | 38,8% |
Reaktionsschritte
5-Oxo-1-(phenylmethyl)-proline (0.176 g, 0.80 mmol, prepared as described below) was dissolved in dichloromethane (3 ml) and to this was added 1-hydroxybenzotriazole (0.119 g, 0.88 mmol), triethylamine (0.113 ml, 0.81 mmol), [(2-chloro-4-fluorophenyl)methyl]amine (0.134 g, 0.84 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.169 g, 0.88 mmol) under an atmosphere of argon. The mixture was stirred at room temperature overnight. The mixture was diluted with dichloromethane and washed sequentially with 2M aqueous hydrogen chloride and saturated aqueous sodium hydrogen carbonate. The organic layer was filtered through a phase separator and then evaporated to give the crude product. The crude material was purified by mass-directed automated HPLC to give pure N-[(2-chloro-4-fluorophenyl)methyl]-5-oxo-1-(phenylmethyl)-prolinamide (0.112 g) as a white solid. LC/MS [M+H]+=361.2, retention time=2.55 minutes.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patentnummer | US08048907B2 |
|---|
| Quelldatensatz | uspto-grants-2011_11 |
|---|
| ORD ID | ord-084ab00bef45435288a2b7abca2ff3f6 |
|---|
| Quellennotiz | uspto-grants-2011_11 |
|---|