6-(IODOACETAMIDO)CAPROIC ACID N-*HYDROXYSUCCINIMIDE synthesis

Yield:134759-23-2 67%

Reaction Conditions:

with dicyclohexyl-carbodiimide in tetrahydrofuran; for 16 h;

Steps:

2

To a solution of 6-(2-iodo-acetylamino)-hexanoic acid (2) (0.20 g, 0.67 mmol) in THF (10 mL) was added N-hydroxysuccinimide (85 mg, 0.74 mmol) and N,N'-dicyclohexylcarbodiimide (0.21 g, 1.0 mmol). The reaction mixture was stirred in the dark for 16 h. When TLC analysis (EtOAc/Hep/AcOH, 80/20/1, v/v/v) revealed complete conversion into the activated ester 3, seven drops of acetic acid were added. The mixture was then stored in the freezer overnight (-20 °C). The crude mixture was filtered and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography (EtOAc/Hep/AcOH, 40/60/5 -> 20/80/5, v/v/v) and concentration of the appropriate fractions gave iV-hydroxysuccinimide ester derivative 3 (0.18 g, 67%). ¹H NMR (MeOD): δ 3.67 (s, 2H), 3.18 (t, 2H), 2.82 (s, 4H), 2.63 (t, 2H), 2.0- 1.0 (m, 6H).

References:

WO2006/82184,2006,A2 Location in patent:Page/Page column 27-28