HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Sodium Carbonate → 2-[2-tert-Butoxycarbonylamino-3-(4-phenyl-cyclohexa-1,5-dienyloxy)-propionylamino]-3-methylbutyric acid methyl ester
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Sodium Carbonate | HCID 10340 | — |
| Edukt | Phenylboronic Acid | HCID 66827 | — |
| Edukt | 2-[3-(4-Bromophenoxy)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-butyric acid methyl ester | HCID 66660903 | — |
| Katalysator | HCID 178418476 | HCID 178418476 | — |
| Lösungsmittel | Toluene | HCID 1140 | — |
| Lösungsmittel | Ethyl Acetate | HCID 8857 | — |
| Produkt | 2-[2-tert-Butoxycarbonylamino-3-(4-phenyl-cyclohexa-1,5-dienyloxy)-propionylamino]-3-methylbutyric acid methyl ester | HCID 66660914 | 64% |
Reaktionsschritte
A solution of 2 M Na2CO3 (4 mL) was added at room temperature under an atmosphere of Argon to a mixture of the compound obtained in Example 22, step f (401 mg, 0.848 mmol), Pd(PPh3)2Cl2 (154 mg, 0.22 mmol) and phenylboronic acid (145 mg, 1.1872 mmol) in toluene (10 mL) and the reaction was heated to reflux. After 5 h, the reaction was cooled to room temperature. The mixture was diluted with EtOAc, and washed with brine. The combined organic layers were dried over anhydrous NaSO4 and concentrated under vacuum. The residue was purified by silica gel column chromatography which gave the title compound as a white solid (255 mg, 64%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08022092B2 |
| Quelldatensatz | uspto-grants-2011_09 |
| ORD ID | ord-3a8fe606011848aeafd0d223340e9377 |
| Quellennotiz | uspto-grants-2011_09 |