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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 516440Erstellt: 25. Oktober 2026

Ethanol → (2R,4R)-5-(3'-Chlorobiphenyl-4-yl)-2-hydroxy-4-{[5-(4-methoxybenzyloxy)-1-methyl-1H-pyrazole-3-carbonyl]amino}pentanoic Acid

https://huagongshe.com/reaction/516440

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktEthanolHCID 702—
EduktWaterHCID 962—
EduktLithium HydroxideHCID 3939—
EduktDimethylformamideHCID 6228—
EduktDiisopropylethylamineHCID 81531—
EduktO-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphateHCID 42624899—
Edukt(2R,4R)-4-amino-5-(3'-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl esterHCID 86682253—
Edukt5-(4-Methoxybenzyloxy)-1-methyl-1H-pyrazole-3-carboxylic AcidHCID 86705138—
Produkt(2R,4R)-5-(3'-Chlorobiphenyl-4-yl)-2-hydroxy-4-{[5-(4-methoxybenzyloxy)-1-methyl-1H-pyrazole-3-carbonyl]amino}pentanoic AcidHCID 8670513970,5%

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

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09108934B2
Quelldatensatzuspto-grants-2015_08
ORD IDord-7ebbacd29781469a942d8344b2262580
Quellennotizuspto-grants-2015_08