반응 #51644

반응 방정식

2-Furancarboxylic acid

carbonyldiimidazole

2-{(1S)-1-Amino-2-[indol-3-yl]ethyl}-4-phenyl-1H-imidazole

→

expected product

수율 94.0%

2-{(1S)-1-[(2-Furanyl)carbonylamino]-2-[indol-3-yl]ethyl}-4-phenyl-1H-imidazole

수율 94.0%

반응 조건

후처리

1. 1
   workup.ADDITIONAminomethylated resin was then added (50-60 mg, 1.2 mmol/g, Novabiochem) in order
2. 2
   기타to quench the excess
3. 3
   기타for about 12 hours
4. 4
   기타Purification on silica gel pad (200 mg, Alltech) with ethyl acetate as eluent

실험 절차

2-Furancarboxylic acid (12.6 mg, 0.11 mmol) was activated overnight at about 22° C. with carbonyldiimidazole (0.11 mmol, 0.2M in chloroform). 2-{(1S)-1-Amino-2-[indol-3-yl]ethyl}-4-phenyl-1H-imidazole (0.1 mmol, 0.5M in chloroform) was added to the media and the mixture was stirred for about 12 hours at about 22° C. Aminomethylated resin was then added (50-60 mg, 1.2 mmol/g, Novabiochem) in order to quench the excess of acylating agent for about 12 hours. Purification on silica gel pad (200 mg, Alltech) with ethyl acetate as eluent gave the expected product (37.2 mg, 94%). 1H-NMR (CDCl3, 100 MHz) δ: 8.36 (br s, 1H); 7.67-6.4 (m, 16H); 5.48 (qd, J=7.1 Hz, 1H); 3.6 (ABX system, 2H). LC/MS: m/z=397 (M+H).

출처