반응 #2130113

반응 방정식

carboxylic acid

2-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)acetic acid

2-amino-1-(thiophen-3yl)ethanone hydrochloride

EDCI

HOBt

HCl

NMM

→

amide

수율 43.3%

2-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)-N-(2-oxo-2-(thiophen-3-yl)ethyl)acetamide

수율 43.3%

용매

DMF

반응 조건

후처리

1. 1
   추출extracted with EtOAc
2. 2
   건조The organic phase was dried over anhydrous MgSO4
3. 3
   여과filtered
4. 4
   기타evaporated under vacuum
5. 5
   기타The residue was further purified by silica column chromatography

실험 절차

To a mixture of the carboxylic acid 55 (1.04 g, 1.5 mmol), 2-amino-1-(thiophen-3yl)ethanone hydrochloride (533 mg, 3.0 mmol), EDCI (575 mg, 3.0 mmol), and HOBt (507 mg, 3.75 mmol) in DMF (10 mL) was added NMM (0.83 mL, 7.5 mmol). The resulting mixture was stirred at room temperature for 15 h. The reaction mixture was poured into a HCl solution (1.0 M, 50 mL), and extracted with EtOAc. The organic phase was dried over anhydrous MgSO4, filtered and evaporated under vacuum. The residue was further purified by silica column chromatography to provide the titled amide compound (529 mg, 0.65 mmol, 43%).

출처