反応 #42409

反応方程式

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

3-oxoindane-5-carboxylic acid

diisopropylethylamine

HATU

→

title compound

N-{(1S,2R)-1-(3,5-Difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-3-oxoindane-5-carboxamide

溶媒

DMF

反応条件

後処理

1. 1
   その他The reaction was partitioned between ethyl acetate and water
2. 2
   洗浄The organic layer is washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine
3. 3
   乾燥dried (sodium sulfate)
4. 4
   ろ過filtered
5. 5
   濃縮concentrated under reduced pressure
6. 6
   その他Purification by flash column chromatography (silica, 8% methanol/methylene chloride)

実験手順

To 3-oxoindane-5-carboxylic acid (2.0 g, 11.5 mmol) in DMF (10 mL) is added diisopropylethylamine (8 mL, 46 mmol), HATU (5.5 g, 14.4 mmol), then (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol dihydrochloride prepared by the method of Example SP-272 (5.6 g, 13.8 mmol). The reaction is stirred 1 h at room temperature. The reaction was partitioned between ethyl acetate and water. The organic layer is washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 8% methanol/methylene chloride) gives the title compound. ESI MS m/z 493.2 [M+H]+.

出典