LAURIC ACID N-HYDROXY-SUCCINIMIDE ESTER

Lauric acid (12.0 g, 60 mmol) dissolved in dry ethyl acetate (100 mL) was added to a solution of N-hydroxysuccinimide (NHS) (6.9 g, 60 mmol) and N, N’-dicyclohexylcarbodiimide (DCC) (12.4 g, 60 mmol) in dry ethyl acetate (300 mL). The reaction mixture was left overnight at room temperature. Dicyclohexylurea (DCU) was removed by filtration and the filtrate was evaporated under reduced pressure to yield white crystals (17.4 g, 95 percent yield). Recrystallization from ethanol yielded 16.6g of pure dodecanoic acid 2, 5-dioxo-pyrrolidine-1-yl ester.Lauric acid (1.2 g, 5.99 mmol, 1 eq) is dissolved in N, N-dimethylformamide (DMF, 70 ml). N, N-disuccinimidyl carbonate (DSC, 4.6 g, 17.97 mmol, 3 eq) and N, N-diisopropylethylamine Hunig base, 10.2 ml, 59.91 mmol, 10 eq), and the mixture was stirred at 40 ° C for 1 hour. After completion of the reaction, the compound was lyophilized to obtain Compound 2-1 (2.1 g, 100percent)

Molecular Weight:297.39
XLogP3:4.4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:12
Exact Mass:297.19400834
Monoisotopic Mass:297.19400834
Topological Polar Surface Area:63.7
Heavy Atom Count:21
Complexity:338
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes