Реакция #76705

Уравнение реакции

dimethylaminopyridine

2-(tert-butoxycarbonylamino)-5-carboxyindan

n-propylamine

triethylamine

→

N-propyl-2-(tert-butoxycarbonylamino)-5-indan carboxamide

Выход 63.6%

Растворители

ethyl acetate

methylene chloride

Условия реакции

Обработка

1. 1
   Промывкаwashed with, in the order of, an aqueous solution of saturated potassium hydrogen sulfate, brine
2. 2
   Сушкаan aqueous solution of saturated sodium hydrogen carbonate, and brine, and then was dried over anhydrous sodium sulfate
3. 3
   ДругоеThe residue obtained
4. 4
   workup.DISTILLATIONby distilling off the solvent under reduced pressure
5. 5
   Другоеwas purified by silica gel chromatography (hexane:ethyl acetate=4:1 to 3:7)

Методика

2-(tert-butoxycarbonylamino)-5-carboxyindan (30 mg, 0.11 mmol) synthesized in Reference Production Example 4, n-propylamine (20 μl, 0.24 mmol), triethylamine (0.20 ml, 1.4 mmol), propanephosphonic acid anhydride (0.3 ml) (see Japanese Unexamined Patent Publication (Kokai) No. 55-100346), and dimethylaminopyridine (acatalytic amount) in methylene chloride (0.25 ml) were stirred at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate, and then washed with, in the order of, an aqueous solution of saturated potassium hydrogen sulfate, brine, an aqueous solution of saturated sodium hydrogen carbonate, and brine, and then was dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=4:1 to 3:7) to obtain N-propyl-2-(tert-butoxycarbonylamino)-5-indan carboxamide (22 mg, 0.070 mmol) having the following physical properties:

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