반응 #69439

반응 방정식

L-valine methyl ester hydrochloride

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

triethylamine

PyBOP

→

title compound

수율 90.4%

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

수율 90.4%

용매

dichloromethane

반응 조건

후처리

1. 1
   세척the mixture was washed saturated NaHCO3 (3×50 mL) and brine (50 mL)
2. 2
   건조dried over MgSO4
3. 3
   농축concentrated
4. 4
   기타The residue was purified by flash chromatography (RediSepRf 80 g)

실험 절차

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).

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