685-88-1, name is Diethyl fluoromalonate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C7H11FO4
Intermediate (5’B) (224.6 g, 698 mmols, 1.0 equiv.), methanol (2250 mL) and diethyl fluoromalonate (187 g, 1050 mmols, 1.5 equiv.) were charged to a suitable reaction vessel equipped with a mechanical stirrer and a digital thermometer. Then sodium methoxide in methanol solution (567 g, 30 wt. %, 3149 mmols, 4.5 equiv.) was charged via an addition funnel while maintaining the reaction temperature 20 to 35 C. The mixture was stirred at 20 to 35 C over 30 min. and a light suspension was obtained. The reaction was complete by HPLC. A solution of 1.5 N HC1 (2300 mL, 3450 mmols, 4.9 equiv.) was charged via an addition funnel over 1 h while maintaining the reaction temperature 20 to 30 C. A white suspension was obtained. The pH of the reaction mixture was to be ~1 by pH paper. The slurry was stirred at 20 to 30 C over 30 min. The resulting slurry was filtered, and the filter cake was washed with a pre-mixed solution of methanol and water (500 mL/500 mL), and then with water (1000 mL). The filter cake was dried under vacuum at 50 to 60 C over 16 h to furnish intermediate (6′) as an off-white solid (264 g, 97% yield, >99% pure by HPLC). – MR (500 MHz, DMSO-d6) delta ppm 12.82 (br. s., 1 H); 12.31 (br. s., 1 H); 9.14 (d, J=1.53 Hz, 1 H); 7.55 (s, 1 H); 7.31 – 7.37 (m, 1 H); 7.18 – 7.25 (m, 1 H); 7.10 – 7.15 (m, 2 H); 6.97 – 7.02 (t, J=7.55 Hz, 1 H); 5.88 (s, 2 H).
The synthetic route of 685-88-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; DUNBAR, Craig Anthony; SETHURAMAN, Vasu; HASHASH, Ahmad; (115 pag.)WO2017/95697; (2017); A1;,
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