반응 #77681

반응 방정식

2-[4-(2-methyl-thiazol-4-yl)-phenoxy]-ethylamine

toluene-4-sulfonic acid 2-(6-acetylamino-pyridin-3-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

diisopropyl ethyl amine

→

desired product

수율 45.0%

(R)-N-[5-(1-(tert-Butyl-dimethyl-silanyloxy)-2-{2-[4-(2-methyl-thiazol-4-yl)-phenoxy]ethylamino}-ethyl)-pyridin-2-yl]-acetamide

수율 45.0%

용매

dimethylsulfoxide

반응 조건

후처리

1. 1
   기타was then partitioned between diethyl ether and water
2. 2
   추출The aqueous phase was extracted with diethyl ether four times
3. 3
   세척the combined organic extracts were then washed with brine
4. 4
   건조dried over magnesium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타The resulting white solid was purified by column chromatography (methylene chloride to 10% methanol/methylene chloride)

실험 절차

In a round-bottomed flask, 2-[4-(2-methyl-thiazol-4-yl)-phenoxy]-ethylamine (175 mg, 0.747 mmol) and toluene-4-sulfonic acid 2-(6-acetylamino-pyridin-3-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester (231 mg, 0.498 mmol) were dissolved in dimethylsulfoxide (0.50 mL), and diisopropyl ethyl amine (0.105 mL, 0.600 mmol) was added in one portion. The resulting mixture was heated to about 80° C. for about sixteen hours, and was then partitioned between diethyl ether and water. The aqueous phase was extracted with diethyl ether four times, and the combined organic extracts were then washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting white solid was purified by column chromatography (methylene chloride to 10% methanol/methylene chloride) to afford 117 mg (45%) of the desired product. LRMS ([M+1]+): 527.1.

출처