反応 #69439

反応方程式

L-valine methyl ester hydrochloride

(1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylic acid

triethylamine

PyBOP

→

title compound

収率 90.4%

N-{[(1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentyl]carbonyl}-L-valine

収率 90.4%

溶媒

dichloromethane

反応条件

後処理

1. 1
   洗浄the mixture was washed saturated NaHCO3 (3×50 mL) and brine (50 mL)
2. 2
   乾燥dried over MgSO4
3. 3
   濃縮concentrated
4. 4
   その他The residue was purified by flash chromatography (RediSepRf 80 g)

実験手順

To a solution of L-valine methyl ester hydrochloride (633 mg, 3.78 mmol), (1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylic acid (755 mg, 3.78 mmol), and triethylamine (1.05 mL, 7.55 mmol) in dichloromethane (30 mL) was added PyBOP (2.95 g, 5.67 mmol). After stirring at rt overnight, the mixture was washed saturated NaHCO3 (3×50 mL) and brine (50 mL), dried over MgSO4, and concentrated. The residue was purified by flash chromatography (RediSepRf 80 g) using 0-40% EtOAc/hexane gradient, affording the title compound (1.04 g, yield 86%): 1H NMR (500 MHz, CDCl3) δ 6.50 (d, J=8.6, 1H), 5.40 (d, J=6.0, 1H), 4.55 (dd, J=4.7, 8.8, 1H), 3.92 (m, 1H), 3.77 (s, 3H), 3.47 (s, 3H), 2.96-2.91 (m, 1H), 2.52-2.46 (m, 1H), 2.38-2.32 (m, 1H), 2.24-2.17 (m, 2H), 2.07-2.01 (m, 1H), 0.97 (d, J=6.9, 3H), 0.92 (d, J=6.9, 3H).

出典