Pyridine → HCID 9880105, compound

Participants

Reaction Steps

1 eq of Wang-O—NH2 is shaken with 11 eq of terephthalic acid, 5.5 eq N,N′-diisopropylcarbodiimide, 5.5 eq 1-hydroxybenzotriazole and 25 eq diisopropylethylamine in DMF for 4 h at 25° C. After that, the resin is washed with DMF (5 times), MeOH (3 times), THF (3 times), CH2Cl2 (3 times) and diethylether (3 times). The resin is then shaken with 5 eq pentafluorophenyl trifluoroacetate and 10 eq pyridine. After that, the resin is washed with DMF (2 times), followed by CH2Cl2 (2 times), followed by diethylether (2 times). The resin is then shaken with 5 eq of naphtalenemethylamine, 10 eq of diisopropylethylamine and leq of 1-hydroxybenzotriazole. It is then shaken with 5 eq pentafluorophenyl trifluoroacetate and 10 eq pyridine. After that, the resin is washed with DMF (2 times), followed by CH2Cl2 (2 times). To liberate the product from the solid support, the resin is shaken with 50% TFA in dry CH2Cl2 with 5% triisopropylsilane added at rt for 1 h. The liquid phase is filtered, the resin washed with CH2Cl2 (3 times), and the combined filtrates are evaporated. The crude product is dissolved in tert-butanol/H2O (80:20) and freeze-dried. To neutralize any remaining TFA, 100 μL of a 25% NH4OH-sol is added and freeze-dried, again. The remaining solid is purified by preparative LC-MS to N-hydroxy-N′-naphthalen-1-ylmethyl-terephthalamide, MS (APCI): 321.1 (M+1)

Provenance & Evidence