Reaktion #557945

Reaktionsgleichung

citric acid

2-chloro-4-fluoro-3-methylbenzonitrile

H-D-Ser-OH

K2CO3

→

final product

Ausbeute 29.3%

(R)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxypropanoic acid

Ausbeute 29.3%

Lösungsmittel

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to room temperature
2. 2
   workup.STIRRINGstirred for 10 min at room temperature
3. 3
   ExtraktionThe solution was extracted with EtOAc several times
4. 4
   Sonstigeto get the crude product
5. 5
   SonstigeThe crude product was chromatographed with a gradient of hexanes/EtOAc

Vorschrift

2-chloro-4-fluoro-3-methylbenzonitrile (500 mg, 2.95 mmol) was mixed together with H-D-Ser-OH (682 mg, 6.49 mmol) in DMSO (20 mL). K2CO3 (856 mg, 6.19 mmol) was added to the reaction mixture and stirred at 75° C. for 24 h. The reaction mixture was cooled to room temperature and poured slowly in to a 10% citric acid solution and stirred for 10 min at room temperature. The solution was extracted with EtOAc several times to get the crude product. The crude product was chromatographed with a gradient of hexanes/EtOAc and then with EtOAc, 100% to give the final product (220 mg): 1H NMR (500 MHz, DMSO-d6, δ in ppm) 7.47 (d, J=9 Hz, 1H), 6.57 (d, J=9 Hz, 1H), 6.13 (br s, 1H), 3.62 (m, 2H), 2.18 (s, 3H).

Quelle