FMOC-12-AMINODODECANOIC ACID synthesis
- Product Name:FMOC-12-AMINODODECANOIC ACID
- CAS Number:128917-74-8
- Molecular formula:C27H35NO4
- Molecular Weight:437.57
82911-69-1
693-57-2
128917-74-8
GENERAL STEPS: 9-Fluorenylmethyl-N-succinimidyl carbonate (Fmoc-OSu, 6.55 g, 21.9 mmol) and sodium bicarbonate (NaHCO3, 2.39 g, 28.5 mmol) were added to a mixture of acetone (90 mL) and water (90 mL) of 12-aminodododecanoic acid (4.71 g, 21.9 mmol). The reaction mixture was stirred at room temperature for 20 hours. Upon completion of the reaction, the pH was adjusted to 4-5 with concentrated hydrochloric acid (HCl) to quench the reaction, followed by extraction of the resulting precipitate with ethyl acetate (EtOAc, 3 x 50 mL). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: hexane-ethyl acetate, 3:1) to afford FMOC-12-aminododecanoic acid (4.20 g, 43% yield) as a white solid. The structure of the product was confirmed by 1H NMR and 13C NMR [28].
82911-69-1
648 suppliers
$7.00/25g
693-57-2
174 suppliers
$11.19/5G
128917-74-8
90 suppliers
$21.00/250mg
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]
28920-43-6
549 suppliers
$5.00/5g
693-57-2
174 suppliers
$11.19/5G
128917-74-8
90 suppliers
$21.00/250mg