HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Methanol → 2-Hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetic acid
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Methanol | HCID 887 | — |
| Edukt | Lithium Hydroxide | HCID 3939 | — |
| Edukt | (R/S)-Ethyl 2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetate | HCID 68232676 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Produkt | 2-Hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetic acid | HCID 67458957 | 73,4% |
Reaktionsschritte
(R/S)-Ethyl 2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetate (150 mg, 0.327 mmol) was dissolved in THF (2 mL) at 0° C. and MeOH (0.5 mL) and 1N LiOH (0.327 mL, 0.327 mmol) were added. After stirring for 1 h, the solution was concentrated and then EtOAc was added. The EtOAc was washed with 1 N HCl aqueous. The organic layer was dried (MgSO4), filtered and concentrated to give (R/S)-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetic acid Int-V (110 mg, 0.240 mmol, 73.4% yield): LCMS=431.9[M+H]+, 1H NMR (400 MHz, methanol-d4) δ ppm 8.19 (2 H, d, J=8.79 Hz), 7.51-7.79 (7 H, m), 5.26 (1 H, s).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08835470B2 |
| Quelldatensatz | uspto-grants-2014_09 |
| ORD ID | ord-46498fbb1b3e47d8bb00f11eb1320e77 |
| Quellennotiz | uspto-grants-2014_09 |