Water → HCID 54209259, Verbindung

HRID 899058

Reaktionsgleichung

C([Li])CCC.[C:6]([O:10][C:11](=[O:32])[CH:12](P(OCC)(OCC)=O)[CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])([CH3:9])([CH3:8])[CH3:7].[C:33]([O:37][C:38](=[O:48])[NH:39][C:40]1[CH:45]=[C:44]([CH:46]=O)[CH:43]=[CH:42][N:41]=1)([CH3:36])([CH3:35])[CH3:34].O>C1COCC1>[C:6]([O:10][C:11](=[O:32])[C:12](=[CH:46][C:44]1[CH:43]=[CH:42][N:41]=[C:40]([NH:39][C:38]([O:37][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:48])[CH:45]=1)[CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])([CH3:7])([CH3:8])[CH3:9]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Butyllithium (1.6 M in hexane, 14.8 ml, 23.7 mmol) was added dropwise to a solution of 2-(diethoxy-phosphoryl)-succinic acid 4-benzyl ester 1-tert-butyl ester (9.50 g, 23.7 mmol in THF (75 mL) at 0° C. under nitrogen. After stirring at 0° C. for 1 h, the solution was transferred to a solution of (4-Formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (3.70 g, 16.6 mmol) in THF (75 mL). The resulting reaction mixture was stirred at 0° C. for 1 h before being allowed to warm to 25° C., and the mixture was stirred overnight. Water (400 mL) was added and the product extracted with CH2Cl2 (3×50 mL). The combined organic layers were dried and concentrated. Flash chromatography (hexane/EtOAc, 4:1) gave 2-(2-tert-Butoxycarbonylamino-pyridin-4-ylmethylene)-succinic acid 4-benzyl ester 1-tert-butyl ester 4.30 g (55%).

Aufarbeitung

customThe resulting reaction mixture
stirringwas stirred at 0° C. for 1 h
temperatureto warm to 25° C.
stirringthe mixture was stirred overnight
extractionthe product extracted with CH2Cl2 (3×50 mL)
customThe combined organic layers were dried
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-c68fb595492a4f2a8a773f285469c50f
Quelldatensatz: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07354895B1

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