HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Dicyclohexylcarbodiimide → HCID 58556961, Verbindung
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Edukt | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Edukt | 3-Quinuclidinol, (-)- | HCID 91404 | — |
| Edukt | (4-Fluoro-phenyl)-(3-fluoro-phenylamino)-acetic acid | HCID 54890833 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Produkt | HCID 58556961 | HCID 58556961 | 50% |
Reaktionsschritte
A mixture of (4-fluoro-phenyl)-(3-fluoro-phenylamino)-acetic acid (I83) (510 mg, 1.94 mmol), (R)-quinuclidin-3-ol (246 mg, 1.94 mmol), HOBT (356 mg, 2.32 mmol) and DCC (480 mg, 2.32 mmol) in THF (10 mL) is stirred at RT overnight (UPLC-MS monitoring: complete conversion). The solvent is evaporated, the crude is dissolved in EtOAc and the insoluble is filtered off. The clear solution is washed with 1N K2CO3 and then with brine. The organic layer is dried over Na2SO4, filtered and evaporated. The crude is purified by silica gel chromatography (EtOAc/MeOH=8/2) to give the title compound as a yellow oil (360 mg, 50% yield, mixture of diastereoisomers).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08835682B2 |
| Quelldatensatz | uspto-grants-2014_09 |
| ORD ID | ord-8bca5f053377479a86f0ce21ea4d3066 |
| Quellennotiz | uspto-grants-2014_09 |