N-DIHYDROCINNAMOYLAMINOCAPROIC ACID, N-HYDROXYSUCCINIMIDE ESTER synthesis

Yield:334616-48-7 72%

Reaction Conditions:

with pyridine in acetonitrile at 20; for 2.5 h;

Steps:

Disuccinimidyl carbonate (155 mg, 604 μmoles) was added to a solution of 31 (159 mg, 604 μmoles) and pyridine (97.7 μL, 1.21 mmoles) in acetonitrile (1 mL). The reaction mixture was stirred at room temperature for 2.5 h, during which the solution became clear and evolved gas. The solution was added to ethyl acetate (5 mL), washed with 1 N HCl (2 x 1 mL) and saturated aqueous NaHCO₃ (2 x 1 mL), dried over MgSO₄, and concentrated in vacuo to yield a colorless oil (156 mg, 433 μmoles, 72%). LRMS: not performed. ¹H NMR: spectrum is consistent with the predicted structure.

References:

EP1235851,2006,B1 Location in patent:Page/Page column 52