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

HRID 226216

Reaktionsgleichung

[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:3][C:4](=[O:6])[OH:5].O[N:25]1[C:29](=[O:30])[CH2:28][CH2:27][C:26]1=[O:31].C1(N=C=NC2CCCCC2)CCCCC1>CCOC(C)=O>[O:31]=[C:26]1[CH2:27][CH2:28][C:29](=[O:30])[N:25]1[O:6][C:4](=[O:5])[CH2:3][CH:2]([NH:1][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

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.

Aufarbeitung

customWhite precipitate began forming
temperatureto warm to rt
stirringAfter stirring for 6 h. at rt the mixture
filtrationwas filtered
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-e3db878e444d437794e28b882efd8c39
Quelldatensatz: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07557137B2

Verknüpfte Notizen

Wird geladen…