反应 #1244320

反应方程式

(S)-1-(benzyloxy carbonyl)-2-piperidinecarboxylic acid

3-amino-5-fluoro-4-hydroxy-pentanoic acid tert-butyl ester

HOBt

EDC

→

sub-title compound

收率 89.0%

5-Fluoro-4-hydroxy-3-[1-(benzyloxycarbonyl)-2-piperidinecarboxamido]-pentanoic acid tert-butyl ester

收率 89.0%

溶剂

THF

反应条件

后处理

1. 1
   workup.ADDITIONwas added
2. 2
   浓缩before being concentrated under reduced pressure
3. 3
   其他The residue was purified by flash chromatography (60% ethyl acetate in hexane)

实验过程

A stirred mixture of (S)-1-(benzyloxy carbonyl)-2-piperidinecarboxylic acid (4.82 g, 18.31 mmol), 3-amino-5-fluoro-4-hydroxy-pentanoic acid tert-butyl ester (3.99 g, 19.25 mmol), HOBt (2.72 g, 20.13 mmol), DMAP (2.57 g, 21.04 mmol) and anhydrous THF (60 ml) was cooled to 0° C. before EDC (3.86 g, 20.13 mmol) was added. The mixture was allowed to warm to room temperature over 16 hrs before being concentrated under reduced pressure. The residue was purified by flash chromatography (60% ethyl acetate in hexane) to afford the sub-title compound as a white foam (7.3754 g, 72%): 1H NMR (400 MHz, CDCl3) δ 1.31-1.80 (14H, m), 2.20-2.38 (1H, m), 2.49-3.07 (3H, m), 3.11-3.70 (1H, m), 3.80-4.58 (4H, m), 4.70-5.28 (1H, m), 6.58-7.05 (1H, m), 7.23-7.48 (5H, m).

来源