تفاعل #92024
ord-01a1af46bf1b41eeb2c2a20afd706a54
معادلة التفاعل
المتفاعلات
ظروف التفاعل
المعالجة
- 1درجة الحرارةThen, the reaction mixture was cooled to room temperature
- 2أخرىto afford a cloudy suspension
- 3استخلاصThen, the organic compound was extracted with ethyl acetate (2×100 mL)
- 4غسيلThe combined extracts were washed with brine solution (100 mL)
- 5تجفيفdried over anhydrous magnesium sulfate
- 6ترشيحFiltration of the drying agent and concentration of the solvent
- 7أخرىgave the crude product which
- 8أخرىwas purified
الإجراء التجريبي
To a suspension of (S)-2-(4-bromo-2,6-difluorobenzoylamino)-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester (5.78 g, 10 mmol), zinc cyanide (940 mg, 8 mmol), and tetrakis(triphenylphosphine)palladium (1.16 g, 1 mmol) in DMF (40 mL, distilled and degassed) at room temperature. The resulting solution was heated to 85° C. and stirred for 24 h at which time TLC analysis of the mixture indicated the absence of starting material. Then, the reaction mixture was cooled to room temperature and it was poured into water (100 mL) to afford a cloudy suspension. Then, the organic compound was extracted with ethyl acetate (2×100 mL). The combined extracts were washed with brine solution (100 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the solvent gave the crude product which was purified using an ISCO (150 g) column chromatography to afford 5.2 g (99% yield) of (S)-2-(4-cyano-2,6-difluorobenzoylamino)-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester as an amorphous white solid. ES-HRMS m/e calcd for C27H26F2N4O5(M+H)+ 525.1944, found 525.1942.