2,3-Dihydroxybutanedioic Acid → HCID 86589095, compound

Participants

Reaction Steps

An alternative synthesis of the title compound. 2-(Chloromethyl)benzimidazole (11.95 g, 71.7 mmol) in 50 mL of N-methylpyrrolidone was treated with 1-(2-pyridyl)piperazine (12.88 g, 78.9 mmol) at 0° C. After one hour, the mixture was treated with triethylamine (7.98 g, 78.9 mmol) and allowed to warm to room temperature. After stirring for 22 hours, the mixture was treated with (L) tartaric acid (24.8 g, 165 mmol) in 50 mL of water. After addition was complete, the mixture was heated at 80° C. for one hour and then allowed to cool to room temperature. The mixture was filtered and the solids were washed with 100 mL of ethanol. The obtained solid was dried under reduced pressure to provide 38.1 g of the title compound as a solid. Elemental analysis calc'd for C25H31N5O12: C 50.59; H, 5.26; N, 11.80; O, 32.35. Found: C, 50.48; H, 5.27; N, 11.78; O, 32.41. DSC: sharp endotherm at 206° C.

Provenance & Evidence