Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Water | HCID 962 | — |
| Edukt | Lithium Hydroxide | HCID 3939 | — |
| Edukt | Dimethylformamide | HCID 6228 | — |
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| 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 5-methyl-2-oxo[1,3]dioxol-4-ylmethyl ester | HCID 86705143 | — |
| Edukt | HCID 178524632 | HCID 178524632 | — |
| Produkt | HCID 178523854 | HCID 178523854 | 58,4% |
Reaktionsschritte
5-Hydroxy-1-pyridin-2-yl-1H-pyrazole-3-carboxylic acid (59.0 mg, 287 μmol) and HCTU (131 mg, 316 μmol) were combined in DMF (1.3 mL, 17.2 mmol). and stirred at room temperature for 15 minutes. (2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid 5-methyl-2-oxo[1,3]dioxol-4-ylmethyl ester (100 mg, 0.3 mmol) and DIPEA (150 μL, 862 μmol) were added, and the resulting mixture was stirred at room temperature for 15 minutes. The reaction was evaporated under reduced pressure. The residue was dissolved in EtOH and a solution of 1 M LiOH in water (1.4 mL, 1.4 mmol) was added. The resulting mixture was stirred at room temperature for 1 hour, then evaporated under reduced pressure. The residue was purified by preparative HPLC to yield the title compound (85 mg). MS m/z [M+H]+ calc'd for C26H23ClN4O5, 507.14. found 507.1.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patentnummer | US09108934B2 |
|---|
| Quelldatensatz | uspto-grants-2015_08 |
|---|
| ORD ID | ord-ce0445d45c554fd1a3e844e7cd261934 |
|---|
| Quellennotiz | uspto-grants-2015_08 |
|---|