反応 #1884985

反応方程式

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

lithium hydroxide monohydrate

hydrochloric acid

→

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

収率 100.2%

溶媒

ethyl acetate

tetrahydrofuran

water

反応条件

後処理

1. 1
   洗浄washed with water (3×) and brine
2. 2
   乾燥dried over anhydrous sodium sulfate
3. 3
   ろ過filtered
4. 4
   濃縮concentrated under vacuum

実験手順

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).

出典