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ChemicalBook CAS DataBase List FMOC-12-AMINODODECANOIC ACID

FMOC-12-AMINODODECANOIC ACID synthesis

2synthesis methods
-

Yield: 43%

Reaction Conditions:

with sodium hydrogencarbonate in water;acetone at 20; for 20 h;

Steps:


Fmoc-OSu (6.55 g; 21.9 mmol) and NaHCO3 (2.39 g; 28.5 mmol) were added to a solution of12-aminododecanoic acid (4.71 g; 21.9 mmol) in acetone (90 mL) and water (90 mL), and then themixture was stirred at rt for 20 h. The reaction mixture was quenched with concentrated HCl until pH4-5, and the resulting precipitate was extracted into with EtOAc (3 x 50 mL). The resulting combinedorganic phases were dried with Na2SO4, filtered, and evaporated. The crude product was purifiedon a silica column (Hexane-EtOAc 3:1) to provide Fmoc-12-aminododecanoic acid (4.20 g; 43%) asa white solid. 1H NMR and 13C NMR were as reported [28].

References:

Zimmermann, Tomas;Christensen, Søren Brøgger;Franzyk, Henrik [Molecules,2018,vol. 23,# 6,art. no. 1463]

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