Реакция #69437

Уравнение реакции

Semicarbazide hydrochloride

(1S,2S,4R)-4-carbamoyl-2-methoxycyclopentyl nitrate

bis(2-oxo-3-oxazolidinyl)phosphinic chloride

sodium hydroxide

triethylamine

→

title compound

(1S,2S,4R)-2-methoxy-4-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)cyclopentyl nitrate

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   КонцентрированиеThe solution was concentrated in vacuo
2. 2
   Температураto reflux for 8 hours
3. 3
   ДругоеPurification of the crude product by reversed-phase mass-directed high-performance liquid chromatography

Методика

(1S,2S,4R)-4-carbamoyl-2-methoxycyclopentyl nitrate (example 14, 0.14 g, 0.68 mmol) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (0.19 g, 0.75 mmol) were stirred for 10 minutes in dichloromethane (5 mL) and triethylamine (0.29 mL, 2.1 mmol). Semicarbazide hydrochloride (0.082 g, 0.73 mmol) was added and stirred at room temperature for 4 days. The solution was concentrated in vacuo and brought up in 1 M sodium hydroxide (3 mL, 3.0 mmol) to reflux for 8 hours. Purification of the crude product by reversed-phase mass-directed high-performance liquid chromatography afforded the title compound as a colorless liquid. 1H NMR (500 MHz, CDCl3) δ 1.93-1.98 (m, 1H), 2.34 (dd, J=4.1, 8.3 Hz, 2H), 2.40-2.47 (m, 1H), 2.40-2.47 (m, 1H), 3.42 (quintet, J=6.2 Hz, 1H), 3.50 (s, 3H), 3.93-3.96 (m, 1H), 5.40-5.43 (m, 1H).

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