HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Triethylamine → (S)-2-tert-Butoxycarbonylamino-3-[4-(pyridin-4-yloxy)-phenyl]-propionic acid methyl ester
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | (Pyridin-4-yl)boronic acid | HCID 2734379 | — |
| Edukt | Boc-Tyr-OMe | HCID 7019130 | — |
| Katalysator | Cupric acetate | HCID 8895 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Lösungsmittel | Ethyl Acetate | HCID 8857 | — |
| Produkt | (S)-2-tert-Butoxycarbonylamino-3-[4-(pyridin-4-yloxy)-phenyl]-propionic acid methyl ester | HCID 66922737 | 20,7% |
Reaktionsschritte
(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionic acid methyl ester (8.46 mmol), 4-pyridyl boronic acid (29.6 mmol), Cu(OAc)2 (16.9 mmol), and molecular sieves were suspended in 25 mL of DCM. Triethylamine (59.2 mmol) was added and the mixture stirred at rt for 10 h. The mixture was diluted with ethyl acetate and washed with 10% sodium carbonate (6×). The organic layer was dried and concentrated under reduced pressure. The residue was purified over silica gel (hexanes-EtOAc) to provide (S)-2-tert-Butoxycarbonylamino-3-[4-(pyridin-4-yloxy)-phenyl]-propionic acid methyl ester (653 mg). LC-MS (m/z) 374.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07727983B2 |
| Quelldatensatz | uspto-grants-2010_06 |
| ORD ID | ord-1cad58ca94e541a28a7f5dd0fffe7af6 |
| Quellennotiz | uspto-grants-2010_06 |