반응 #42522

반응 방정식

(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol

1-butyl-1,2,3,4-tetrahydroquinoline-7-carboxylic acid

HBTU

diisopropylethylamine

diisopropylethylamine

→

1-butyl-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-1,2,3,4-tetrahydroquinoline-7-carboxamide

수율 41.5%

용매

methylene chloride

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   세척washed with 1 N hydrochloric acid (10 mL), saturated sodium bicarbonate (10 mL), and brine
2. 2
   건조The organic layer was then dried (magnesium sulfate)
3. 3
   여과filtered
4. 4
   농축concentrated under reduced pressure
5. 5
   기타Purification by flash column chromatography (silica, 1:9 methanol/chloroform)

실험 절차

A solution of 1-butyl-1,2,3,4-tetrahydroquinoline-7-carboxylic acid (134 mg, 0.57 mmol), HBTU (327 mg, 0.86 mmol), and diisopropylethylamine (150 μL, 0.86 mmol) was stirred in methylene chloride (3.0 mL) for 15 min. A solution of (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol (Example SP-272) (234 mg, 0.57 mmol) and diisopropylethylamine (150 μL, 0.86 mmol) in methylene chloride (3.0 mL) was added and the reaction mixture was stirred overnight. The reaction mixture was diluted with methylene chloride, washed with 1 N hydrochloric acid (10 mL), saturated sodium bicarbonate (10 mL), and brine. The organic layer was then dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:9 methanol/chloroform) provided 1-butyl-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-1,2,3,4-tetrahydroquinoline-7-carboxamide (130 mg): ESI MS m/z 550 [M+H]+

출처