반응 #2329611

반응 방정식

Compound 42

(1R,2R,4S)-2-((S)-1-tert-Butoxycarbonyl-butylcarbamoyl)-4-hydroxy-cyclopentanecarboxylic acid methyl ester

2-phenyl-7-methoxy-4-quinolinol

PPh3

DIAD

→

43

수율 78.0%

(1R,2R,4R)-2-((S)-1-tert-Butoxycarbonyl-butylcarbamoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarboxylic acid methyl ester

수율 78.0%

용매

THF

THF

반응 조건

후처리

1. 1
   기타was lowered to 0° C
2. 2
   workup.ADDITIONwas added to the mixture during five minutes
3. 3
   기타Evaporation and purification by flash column chromatography (toluene/EtOAc gradient 6:1 to 4:1)

실험 절차

Compound 42 (249 mg, 0.725 mmol), 2-phenyl-7-methoxy-4-quinolinol (310 mg, 1.23 mmol) and PPh3 (580 mg, 2.21 mmol) were dissolved in dry THF and the temperature was lowered to 0° C. DIAD (435 uL. 2.21 mmol) dissolved in 2 mL dry THF, was added to the mixture during five minutes. After two hours the temperature was raised to room temperature and the solution was stirred overnight. Evaporation and purification by flash column chromatography (toluene/EtOAc gradient 6:1 to 4:1) gave 43 (324 mg, 78%).

출처