反应 #1884985

反应方程式

N-tert-butoxycarbonyl-O-(4-pentenyl)-L-serine, methyl ester

lithium hydroxide monohydrate

hydrochloric acid

→

N-tert-butoxycarbonyl-O-(4-pentenyl)-L-serine

收率 100.2%

溶剂

ethyl acetate

tetrahydrofuran

water

反应条件

后处理

1. 1
   洗涤washed with water (3×) and brine
2. 2
   干燥dried over anhydrous sodium sulfate
3. 3
   过滤filtered
4. 4
   浓缩concentrated under vacuum

实验过程

To a solution of 6.65 g (23 mmol) of N-tert-butoxycarbonyl-O-(4-pentenyl)-L-serine, methyl ester in 500 mL of tetrahydrofuran at room temperature was added a solution of 1.95 g (46 mmol) of lithium hydroxide monohydrate in 100 mL of water. The resulting mixture was stirred at room temperature for 40 hours. To the reaction mixture then was added 46 mL of 1.00N hydrochloric acid. The mixture was diluted with ethyl acetate, washed with water (3×) and brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to afford 6.30 g of N-tert-butoxycarbonyl-O-(4-pentenyl)-L-serine as a colorless oil. NMR (300 MHz, CDCl3): δ 5.77 (d of d of t, 1 H, J=17.2, 10.2, 6.6 Hz), 5.37 (br d, 1 H, J=8.0 Hz), 5.03-4.92 (m, 2 H), 4.42 (m, 1 H), 3.87 (d of d, 1 H, J=9.5, 2.6 Hz), 3.63 (d of d, 1 H, J=9.5, 4.0 Hz), 3.45 (t, 2 H, J=6.6 Hz), 2.07 (quart., 2 H, J=7.3 Hz), 1.64 (quint., 2 H, J=7.3 Hz), 1.44 (s, 9 H).

来源