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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 226216Erstellt: 25. Oktober 2026

Dicyclohexylcarbodiimide → 2-Tert-butoxycarbonylamino-succinic acid 1-benzyl ester 4-(2,5-dioxo-pyrrolidin-1-yl) ester

https://huagongshe.com/reaction/226216

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktDicyclohexylcarbodiimideHCID 10868—
EduktN-HydroxysuccinimideHCID 80170—
Edukt(3S)-4-(benzyloxy)-3-(((tert-butoxy)carbonyl)amino)-4-oxobutanoic acidHCID 7017887—
LösungsmittelEthyl AcetateHCID 8857—
Produkt2-Tert-butoxycarbonylamino-succinic acid 1-benzyl ester 4-(2,5-dioxo-pyrrolidin-1-yl) esterHCID 21844024—

Reaktionsbedingungen

Temperatur0 °C

Reaktionsschritte

A solution of BOC-Asp-OBzl (1.49 g, 4.61 mmol) and N-Hydroxy succinimide (584 mg, 5.07 mmol) in EtOAc (20 ml) was cooled to 0° C. 1,3-Dicyclohexylcarbodiimide (1.05 g, 5.07 mmol) was added portionwise. White precipitate began forming. The resulting mixture was stirred at 0° C. for 10 min. and then allowed to warm to rt. After stirring for 6 h. at rt the mixture was filtered and concentrated in vacuo to give 2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester 4-(2,5-dioxo-pyrrolidin-1-yl) ester as a clear, colorless oil which was used without further purification.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07557137B2
Quelldatensatzuspto-grants-2009_07
ORD IDord-e3db878e444d437794e28b882efd8c39
Quellennotizuspto-grants-2009_07