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HRID 516471Erstellt: 25. Oktober 2026

Acetone → (2R,4R)-4-[(1-Butyryloxymethoxy-1H-[1,2,3]triazole-4-carbonyl)amino]-5-(5'-chloro-2'-fluorobiphenyl-4-yl)-2-hydroxypentanoic Acid

https://huagongshe.com/reaction/516471

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktAcetoneHCID 180—
EduktTriethylamineHCID 8471—
EduktChloromethyl butanoateHCID 2725008—
Edukt(2R,4R)-5-(5'-Chloro-2'-fluorobiphenyl-4-yl)-2-hydroxy-4-[(1-hydroxy-1H-[1,2,3]triazole-4-carbonyl)amino]pentanoic AcidHCID 67969390—
Produkt(2R,4R)-4-[(1-Butyryloxymethoxy-1H-[1,2,3]triazole-4-carbonyl)amino]-5-(5'-chloro-2'-fluorobiphenyl-4-yl)-2-hydroxypentanoic AcidHCID 8670515916,4%

Reaktionsbedingungen

Temperatur65 °C

Reaktionsschritte

Chloromethyl butyrate (13.7 mg, 100 μmol) was added to a solution of (2R,4R)-5-(5′-chloro-2′-fluorobiphenyl-4-yl)-2-hydroxy-4-[(1-hydroxy-1H-1,2,3-triazole-4-carbonyl)amino]pentanoic acid (30.0 mg, 66.8 μmol) in acetone (0.5 mL, 6.8 mmol). Et3N (18.6 μL, 134 μmol) was added and the resulting mixture was stirred at 65° C. for 2 hours. The mixture was then concentrated in vacuo to yield a yellow liquid. The crude liquid was purified (preparative scale C18 column chromatography, small column, using 30-90% MeCN in water with 0.05% TFA) to yield the title compound as a white solid (6.0 mg). MS m/z [M+H]+ calc'd for C25H26ClFN4O7, 549.15. found 549.1.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09108934B2
Quelldatensatzuspto-grants-2015_08
ORD IDord-028a2fca226e4dd79d571027a3a5fdef
Quellennotizuspto-grants-2015_08