Water → HCID 2301708, compound

N,N′-Di-n-butyl L-tartaramide was prepared by the reaction of n-butyl amine with diethyl L-tartrate. Diethyl L-tartrate (20.010 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-Butyl amine (14.906 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, the flask was stoppered and refrigerated at approximately 45° F. (7° C.). The product crystallized out after 30 min of refrigeration; however, it was allowed to remain in the refrigerator for 3 days. The white needle-like crystals were filtered, washed with methanol (˜150 mL), washed with diethyl ether (2×30 mL), and dried under vacuum. The product was obtained in 56% yield (14.275 g, 54.8 mmole).

1. customequipped with a teflon coated magnetic stir bar
2. washto rinse all of the amine into the reaction flask
3. customrefrigerated at approximately 45° F.
4. custom(7° C.)
5. customThe product crystallized out after 30 min of refrigeration
6. waitto remain in the refrigerator for 3 days
7. filtrationThe white needle-like crystals were filtered
8. washwashed with methanol (˜150 mL)
9. washwashed with diethyl ether (2×30 mL)
10. customdried under vacuum
11. customThe product was obtained in 56% yield (14.275 g, 54.8 mmole)

ORD record

ord-e9c8e0d429f3492da71e53691fc2dfce

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06399543B1