Dimethylformamide → 2-Valeramidoisonicotinic acid morpholide

Reaktionsgleichung

[OH:1]N1C2C=CC=CC=2N=N1.[CH:11]1([N:17]=[C:18]=[N:19][CH:20]2CC[CH2:23][CH2:22][CH2:21]2)C[CH2:15][CH2:14][CH2:13][CH2:12]1.N1C[CH2:30][O:29][CH2:28]C1.[CH3:32][N:33]([CH3:36])[CH:34]=[O:35]>>[C:11]([NH:17][C:18]1[CH:23]=[C:22]([CH:21]=[CH:20][N:19]=1)[C:34]([N:33]1[CH2:36][CH2:30][O:29][CH2:28][CH2:32]1)=[O:35])(=[O:1])[CH2:12][CH2:13][CH2:14][CH3:15]

Komponenten

Edukt 4

HCID 6228Dimethylformamide

HCID 8083Morpholine

HCID 10868Dicyclohexylcarbodiimide

HCID 757711-Hydroxybenzotriazole

Produkt 1

HCID 540118162-Valeramidoisonicotinic acid morpholide

Versuchsvorschrift

The compound ([9]-(94)-467') (2.4610 g) prepared in Example 98 was dissolved in anhydrous dimethylformamide (DMF) (37 ml). Then, 1-hydroxybenzotriazole (1.9477 g), N,N'-dicyclohexylcarbodiimide (2.9739 g), and morpholine (1.3 ml) were added to the solution. The mixture was stirred at room temperature for 16 hours. The insolubles were filtered out, and the filtrate was concentrated. The resulting residue was dissolved in chloroform, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain yellowish brown oil (7.4981 g). The crude oil was purified by silica gel column chromatography (Kieselgel 60=230 g, chloroform/acetone=5/1) to obtain the above-captioned compound ([9]-(94)-467") (3.1756 g) as white crystals.