反応 #502132

反応方程式

naproxen

4-mercapto-l-butanol

1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride

4-mercapto-l-butanol

→

(2S)-1-(4-Hydroxybutylthio)-2-(6-methoxy(2-naphthyl))propan-1-one

収率 30.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他partitioned between dichloromethane and water
2. 2
   洗浄the water layer was washed with more dichloromethane
3. 3
   洗浄The combined organic layer was washed with water and brine
4. 4
   乾燥dried over magnesium sulfate
5. 5
   濃縮The solution was concentrated under vacuum
6. 6
   その他the residue was purified via column chromatography, 50% ethyl acetate/hexane
7. 7
   その他the solvent removed by rotary evaporation
8. 8
   その他to give an oil, 2.647 g, which

実験手順

To a solution of naproxen (5.03 g, 21.9 mmol), 4-mercapto-l-butanol (2.32 g, 21.9 mmol) and N,N-dimethylaminopyridine (DMAP) (0.534 g, 4.37 mmol) in dichloromethane (200 mL) at room temperature was added 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (EDAC) (5.03 g, 26.2 mmol) as a solid, in portions. The reaction mixture was stirred for 3 hours at room temperature, then partitioned between dichloromethane and water, and the water layer was washed with more dichloromethane. The combined organic layer was washed with water and brine, then dried over magnesium sulfate. The solution was concentrated under vacuum, and the residue was purified via column chromatography, 50% ethyl acetate/hexane. The appropriate fractions were combined, and the solvent removed by rotary evaporation to give an oil, 2.647 g, which contained 19% 4-mercapto-l-butanol by weight (product weight 2.07 g, 6.5 mmol, 30% yield): 1H NMR (300 MHz, CDCl3) δ 7.73 (d, J=2.7 Hz, 1H), 7.71 (d, J=2.3 Hz, 1H), 7.69 (d, J=1.0 Hz, 1H), 7.40 (dd, J=1.8, 8.5 Hz, 1H), 7.15 (dd, J=2.5, 8.8 Hz, 1H), 7.12 (d, J=2.3 Hz, 1H), 4.02 (q, J=7.1 Hz, 1H), 3.92 (s, 3H), 3.61-3.64 (m, 2H), 2.87 (m, 2H), 1.61 (d, J=7.1 Hz, 3H), 1.59 (m, 2H), 1.41 (m, 2H); mass spectrum (API-TIS) m/z 319 (M+H+), 336 (M+18+).

出典