Reaktion #42575

Reaktionsgleichung

3-Iodo-5-(methoxycarbonyl)benzoic acid

diisopropylethylamine

HATU

N-methylbutylamine

→

title compound

Methyl 3-{[butyl(methyl)amino]carbonyl}-5-iodobenzoate

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction is partitioned between ethyl acetate and water
2. 2
   WaschenThe organic layer is washed with saturated sodium bicarbonate, and saturated sodium chloride
3. 3
   Trocknendried (sodium sulfate)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigePurification by flash column chromatography (silica, 40% ethyl acetate/hexane)

Vorschrift

3-Iodo-5-(methoxycarbonyl)benzoic acid (1 g, 3.3 mmol) is dissolved in DMF (10 mL), and diisopropylethylamine (1.7 mL, 9.8 mmol), HATU (1.5 g, 3.9 mmol), and N-methylbutylamine (581 μL, 4.9 mmol) are added. The reaction stirred at room temperature 2 h. The reaction is partitioned between ethyl acetate and water. The organic layer is washed with saturated sodium bicarbonate, and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 40% ethyl acetate/hexane) provides the title compound. ESI MS m/z 376.1 [M+H]+.

Quelle