HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Trifluoromethanesulfonic acid, lithium salt → methyl (2R)-3-[(4-fluoro-3-methyl-2-oxo-2,3-dihydro-6-benzoxazolyl)amino]-2-hydroxypropanoate
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Trifluoromethanesulfonic acid, lithium salt | HCID 3664839 | — |
| Edukt | Methyl (2R)-2-oxiranecarboxylate | HCID 9877347 | — |
| Edukt | 6-amino-4-fluoro-3-methyl-1,3-benzoxazol-2(3H)-one | HCID 68486035 | — |
| Lösungsmittel | Acetonitrile | HCID 6342 | — |
| Produkt | methyl (2R)-3-[(4-fluoro-3-methyl-2-oxo-2,3-dihydro-6-benzoxazolyl)amino]-2-hydroxypropanoate | HCID 86610080 | 99,6% |
Reaktionsbedingungen
| Temperatur | 90 °C |
|---|
Reaktionsschritte
A mixture of 6-amino-4-fluoro-3-methyl-1,3-benzoxazol-2(3H)-one (Step 7, 0.630 g, 3.46 mmol), methyl (2R)-glycidate (0.353 g, 3.46 mmol) and lithium trifluoromethanesulfonate (0.540 g, 3.46 mmol) in acetonitrile (10 ml) is stirred and heated at 90° C. overnight. The reaction mixture is diluted with ethyl actetate, washed with water and saline, dried (MgSO4), and evaporated under reduced pressure. Final purification by flash column chromatography (50% ethyl acetate/hexane) gives pure product as a white solid (0.98 g, 60%); MS for C12H13FN2O5 m/z 285 (M+H)+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07645781B2 |
| Quelldatensatz | uspto-grants-2010_01 |
| ORD ID | ord-b32c39b814004a17a6d0b63d373785ce |
| Quellennotiz | uspto-grants-2010_01 |