反応 #42353

反応方程式

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

3-[(dipropylamino)carbonyl]-5-[1-(ethoxymethyl)-1H-imidazol-2-yl]benzoic acid

diisopropylethylamine

HBTU

diisopropylethylamine

→

title compound

N1-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-5-[1-(ethoxymethyl)-1H-imidazol-2-yl]-N3,N3-dipropylisophthalamide

溶媒

methylene chloride

methylene chloride

反応条件

後処理

1. 1
   濃縮concentrated under reduced pressure
2. 2
   workup.ADDITIONThe residue is diluted with ethyl acetate (20 mL)
3. 3
   洗浄washed with saturated sodium bicarbonate, and brine
4. 4
   乾燥dried (sodium sulfate)
5. 5
   ろ過filtered
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他Purification by flash column chromatography (silica gel, 5:95 methanol/methylene chloride)

実験手順

To a stirred solution of 3-[(dipropylamino)carbonyl]-5-[1-(ethoxymethyl)-1H-imidazol-2-yl]benzoic acid (177 mg, 0.47 mmol), diisopropylethylamine (651 mg, 0.5 mmol), and HBTU (209 mg, 0.55 mmol) in methylene chloride (5 mL) is added a mixture of (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol prepared by the method of Example SP-272 (196 mg, 0.48 mmol) and diisopropylethylamine (130 mg, 1.0 mmol) in methylene chloride (5 mL). The reaction mixture is stirred at room temperature for 15 h and concentrated under reduced pressure. The residue is diluted with ethyl acetate (20 mL), washed with saturated sodium bicarbonate, and brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 5:95 methanol/methylene chloride) provides the title compound. APCI MS m/z 690.3 [M+H]+.

出典