HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Ethanol → (2R,4R)-5-(3'-Chlorobiphenyl-4-yl)-2-hydroxy-4-{[5-(4-methoxybenzyloxy)-1-methyl-1H-pyrazole-3-carbonyl]amino}pentanoic Acid
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Ethanol | HCID 702 | — |
| 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 ethyl ester | HCID 86682253 | — |
| Edukt | 5-(4-Methoxybenzyloxy)-1-methyl-1H-pyrazole-3-carboxylic Acid | HCID 86705138 | — |
| Produkt | (2R,4R)-5-(3'-Chlorobiphenyl-4-yl)-2-hydroxy-4-{[5-(4-methoxybenzyloxy)-1-methyl-1H-pyrazole-3-carbonyl]amino}pentanoic Acid | HCID 86705139 | 70,5% |
Reaktionsschritte
5-(4-Methoxy-benzyloxy)-1-methyl-1H-pyrazole-3-carboxylic acid (118.8 mg, 453 mol) was combined with HCTU (187.3 mg, 453 μmol) and DMF (2.0 mL, 25.9 mmol). The mixture was stirred at room temperature for 15 minutes. DIPEA (225 μL, 1.3 mmol) and (2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester (150 mg, 430 μmol) were added and the mixture was stirred at room temperature for 15 minutes. The solvent was removed in vacuo. EtOH (1.5 mL, 25.9 mmol) was added, followed by a solution of 1 M LiOH in water (4.3 mL, 4.3 mmol). The mixture was stirred at room temperature for 1 hour. The solvent was removed in vacuo and the product was purified by reverse phase chromatography to yield the title compound (171 mg).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09108934B2 |
| Quelldatensatz | uspto-grants-2015_08 |
| ORD ID | ord-7ebbacd29781469a942d8344b2262580 |
| Quellennotiz | uspto-grants-2015_08 |