HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Ethanol → (2R,4R)-5-(3'-Chlorobiphenyl-4-yl)-2-hydroxy-4-[(3-methoxyisoxazole-5-carbonyl)amino]pentanoic Acid
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Ethanol | HCID 702 | — |
| Edukt | Water | HCID 962 | — |
| Edukt | Lithium Hydroxide | HCID 3939 | — |
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | 3-Methoxy-1,2-oxazole-5-carboxylic acid | HCID 327717 | — |
| Edukt | O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate | HCID 42624899 | — |
| Edukt | (2R,4R)-4-amino-5-(3'-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester | HCID 86682253 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | (2R,4R)-5-(3'-Chlorobiphenyl-4-yl)-2-hydroxy-4-[(3-methoxyisoxazole-5-carbonyl)amino]pentanoic Acid | HCID 67969790 | — |
Reaktionsschritte
3-Methoxyisoxazole-5-carboxylic acid (39.4 mg, 275 μmol) and HCTU (128 mg, 310 μmol) were combined in DMF, and stirred for 10 minutes at room temperature. DIPEA (72 μL, 413 μmol) and (2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester (50 mg, 0.1 mmol) were added, and the resulting mixture was stirred at room temperature overnight. The mixture was combined with EtOH (402 μL, 6.9 mmol) and 1 M LiOH in water (1.1 mL, 1.1 mmol). The mixture was stirred at room temperature for 1 hour, evaporated under reduced pressure, and purified by preparative HPLC to yield the title compound. MS m/z [M+H]+ calc'd for C22H21ClN2O6, 445.11. found 445.2.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09108934B2 |
| Quelldatensatz | uspto-grants-2015_08 |
| ORD ID | ord-410b66b9e03742bdb920b2c196790c3d |
| Quellennotiz | uspto-grants-2015_08 |