Water → HCID 13226340, compound

N,N′-Di-n-propyl L-tartaramide was prepared by the reaction of n-propyl amine with diethyl L-tartrate. Diethyl L-tartrate (20.027 g, 1.0 eq) and HPLC grade methanol (40 mL) were weighed into a 250 mL round-bottomed flask equipped with a teflon coated magnetic stir bar. n-Propyl amine (12.038 g, 2.0 eq) was slowly poured into the stirring diethyl L-tartrate solution. Some fuming and a color change from water-white to pale yellow were observed. Additional methanol (10 mL) was used to rinse all of the amine into the reaction flask. After stirring the solution for 30 min at ambient temperature, the product began to crystallize from solution. The reaction mixture was allowed to sit at ambient temperature for two hours. The flat, white crystals were filtered, washed with methanol (2×50 mL), washed with diethyl ether (2×30 mL), and dried under vacuum. The first crop of product was obtained in 35% yield (7.977 g, 34.34 mmole). Subsequently, a second crop of crystals (1.80 g, 7.75 mmole) was isolated from the mother liquor.

1. customequipped with a teflon coated magnetic stir bar
2. washto rinse all of the amine into the reaction flask
3. customto crystallize from solution
4. waitto sit at ambient temperature for two hours
5. filtrationThe flat, white crystals were filtered
6. washwashed with methanol (2×50 mL)
7. washwashed with diethyl ether (2×30 mL)
8. customdried under vacuum
9. customThe first crop of product was obtained in 35% yield (7.977 g, 34.34 mmole)

ORD record

ord-c087d2e4e5f64b5db4c811af3fa290a5

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06399543B1