Zurück
HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1265589Erstellt: 26. Oktober 2026

Aldoxime → 3-[2-(3-Methyl-isoxazol-5-yl)-pyridin-4-yl]-3-oxo-propionic acid tert.-butyl ester

https://huagongshe.com/reaction/1265589

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktAldoximeHCID 7863—
EduktPotassium CarbonateHCID 11430—
EduktChlorosuccinimideHCID 31398—
EduktTrimethylsilylacetyleneHCID 66111—
EduktMethyl 2-iodoisonicotinateHCID 196869—
Edukt2-(3-Methyl-isoxazol-5-yl)-isonicotinic acid methyl esterHCID 69687972—
EduktLithium Tert-butyl AcetateHCID 86586795—
LösungsmittelMethanolHCID 887—
LösungsmittelPyridineHCID 1049—
LösungsmittelChloroformHCID 6212—
LösungsmittelTriethylamineHCID 8471—
Produkt3-[2-(3-Methyl-isoxazol-5-yl)-pyridin-4-yl]-3-oxo-propionic acid tert.-butyl esterHCID 69688172—

Reaktionsschritte

The title compound was prepared from 2-(3-methyl-isoxazol-5-yl)-isonicotinic acid methyl ester [prepared by i.) reaction of 2-iodo-isonicotinic acid methyl ester [CAS-No. 134579-47-8] with trimethylsilylacetylene according to general procedure H; ii.) desilylation by reaction with cat. K2CO3 in MeOH at 0° C. for 4 h; iii.) cycloadditon with a mixture of NCS, acetaldoxime, Et3N and cat. amount of pyridine in CHCl3 at 50° C. according to Tetrahedron 1984, 40, 2985-2988] by treatment with lithium tert.-butyl acetate according to general procedure K (method b). Obtained as a brown solid (5.17 g).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS06544985B2
Quelldatensatzuspto-grants-2003_04
ORD IDord-ecde33b9de96434a94df97d29cff0ae0
Quellennotizuspto-grants-2003_04