반응 #76705

반응 방정식

dimethylaminopyridine

2-(tert-butoxycarbonylamino)-5-carboxyindan

n-propylamine

triethylamine

→

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

수율 63.6%

용매

ethyl acetate

methylene chloride

반응 조건

후처리

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

실험 절차

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:

출처