Reaktion #1195906

Reaktionsgleichung

1-Hydroxybenzotriazole

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole-6-carboxylic acid

hydroxylamine hydrochloride

diisopropylethylamine

→

1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole-6-carbohydroxamic acid

Ausbeute 64.6%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirred at 20° C. for 2 hours
2. 2
   Sonstigethe reaction mixture was partitioned between ethyl acetate and water
3. 3
   WaschenThe organic phase was washed with 1N hydrochloric acid and brine
4. 4
   Trocknendried over sodium sulfate
5. 5
   Sonstigeevaporated in vacuo
6. 6
   SonstigeThe residue was purified by preparative thin layer chromatography with 10% methanol in chloroform and recrystallization from ethyl acetate

Vorschrift

1-Hydroxybenzotriazole (68 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (72 mg) were added to a solution of 1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole-6-carboxylic acid (100 mg) in dimethylformamide (3 ml), and the mixture was stirred at 20° C. overnight, then hydroxylamine hydrochloride (35 mg) and diisopropylethylamine (0.088 ml) were added. After stirred at 20° C. for 2 hours, the reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with 1N hydrochloric acid and brine, dried over sodium sulfate, and evaporated in vacuo. The residue was purified by preparative thin layer chromatography with 10% methanol in chloroform and recrystallization from ethyl acetate to give 1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole-6-carbohydroxamic acid (67 mg) as pale red crystals.

Quelle