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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 516466Erstellt: 25. Oktober 2026

Ethanol → (2R,4R)-5-(3'-Chlorobiphenyl-4-yl)-2-hydroxy-4-[(3-methoxyisoxazole-5-carbonyl)amino]pentanoic Acid

https://huagongshe.com/reaction/516466

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktEthanolHCID 702—
EduktWaterHCID 962—
EduktLithium HydroxideHCID 3939—
EduktDiisopropylethylamineHCID 81531—
Edukt3-Methoxy-1,2-oxazole-5-carboxylic acidHCID 327717—
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—
LösungsmittelDimethylformamideHCID 6228—
Produkt(2R,4R)-5-(3'-Chlorobiphenyl-4-yl)-2-hydroxy-4-[(3-methoxyisoxazole-5-carbonyl)amino]pentanoic AcidHCID 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

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09108934B2
Quelldatensatzuspto-grants-2015_08
ORD IDord-410b66b9e03742bdb920b2c196790c3d
Quellennotizuspto-grants-2015_08