p-Toluenesulfonic acid → HCID 178472044, Verbindung

Temperatur

-15 °C

Next, this crude ethyl 2-(2,6-dichloronicotinoyl)-3-ethoxyacrylate (2.11 g, 6.62 mmol) and the para-toluenesulfonic acid salt of 2-(S)-fluoro-1-(R)-cyclopropylamine (2.45 g, 9.91 mmol) were suspended in dichloromethane (30 ml), and triethylamine (2.77 ml, 19.87 mmol) was added dropwise gradually thereto while stirring at −15° C. After completion of dripping, the reaction solution was stirred at room temperature for 15 hours. After adding ethyl acetate (100 ml) to the reaction solution, the organic layer was washed with a 10% aqueous citric acid solution (80 ml), saturated sodium bicarbonate water (80 ml), and saturated saline solution (80 ml), in that order, and then dried over anhydrous sodium sulfate. After filtering, the filtrate was concentrated under a reduced pressure, and 2.10 g (90%, 2 processes) of the title compound was thereby obtained as a yellowish-brown, oily substance (E/Z mixture). This resulting substance was used in the subsequent reaction without further purification.

1. stirringthe reaction solution was stirred at room temperature for 15 hours
2. washthe organic layer was washed with a 10% aqueous citric acid solution (80 ml), saturated sodium bicarbonate water (80 ml), and saturated saline solution (80 ml), in that order
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationAfter filtering
5. concentrationthe filtrate was concentrated under a reduced pressure, and 2.10 g (90%, 2 processes) of the title compound
6. customwas thereby obtained as a yellowish-brown, oily substance (E/Z mixture)
7. customThis resulting substance was used in the subsequent reaction without further purification

ORD-Eintrag

ord-ec391f2c158c4e1eb9366ef3019cd7b5

Quelldatensatz

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07902226B2