반응 #484369

반응 방정식

rac-(cyclohex-2-enyloxy)-(3,4-dichloro-phenyl)-acetic acid

BOP reagent

triethylamine

2-aminothiazole

→

rac-(cyclohex-2-enyloxy)-2-(3,4-dichloro-phenyl)-N-thiazol-2-yl-acetamide

수율 92.2%

용매

water

dichloromethane

반응 조건

후처리

1. 1
   추출extracted with ethyl acetate (3×15 mL)
2. 2
   세척The combined organic layers were washed with water (1×10 mL), 1N sodium hydroxide solution (1×10 mL), 1N hydrochloric acid (1×10 mL), and brine (1×10 mL)
3. 3
   건조were dried over sodium sulfate
4. 4
   기타evaporated in vacuo
5. 5
   기타The residue was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 95/5 hexanes/ethyl acetate)

실험 절차

A solution of rac-(cyclohex-2-enyloxy)-(3,4-dichloro-phenyl)-acetic acid (89 mg, 0.28 mmol) in dichloromethane (10 mL) was treated with BOP reagent (187 mg, 0.42 mmol), triethylamine (0.12 mL, 0.85 mmol), and 2-aminothiazole (42 mg, 0.42 mmol) at 25° C. The resulting brownish-orange solution was then stirred 16 h at 25° C., then was diluted with water (10 mL) and extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with water (1×10 mL), 1N sodium hydroxide solution (1×10 mL), 1N hydrochloric acid (1×10 mL), and brine (1×10 mL), then were dried over sodium sulfate and evaporated in vacuo. The residue was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 95/5 hexanes/ethyl acetate) to provide rac-(cyclohex-2-enyloxy)-2-(3,4-dichloro-phenyl)-N-thiazol-2-yl-acetamide (99 mg, 92% yield) as a white foam: EI-HRMS m/e calcd for C17H16Cl2O2N2S (M+) 382.0309, found 382.0308.

출처