反应 #87188

反应方程式

(S)-2-((tert-butoxycarbonyl)amino)-3-(pyridin-2-yl)propanoic acid

BnCOCl

→

(S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-(pyridin-2-yl)propanoate

收率 42.0%

溶剂

DCM

反应条件

后处理

1. 1
   温度to warm to ambient temperature overnight at which time it
2. 2
   其他was quenched with sodium bicarbonate (sat.)
3. 3
   萃取extracted with ethyl acetate (2×)
4. 4
   干燥dried with sodium sulfate
5. 5
   过滤filtered
6. 6
   浓缩concentrated
7. 7
   其他Purification by column chromatography (0-50% ethyl acetate/hexanes+1% TEA)

实验过程

To (S)-2-((tert-butoxycarbonyl)amino)-3-(pyridin-2-yl)propanoic acid (1.00 g, 3.76 mmol) in DCM (10 mL) was added TEA (0.974 mL, 7.52 mmol) and DMAP (23 mg, 0.188 mmol) and the reaction mixture was cooled to 0° C. and BnCOCl (635 mL, 4.51 mmol) was added via an addition funnel over 20 min. The mixture was allowed to warm to ambient temperature overnight at which time it was quenched with sodium bicarbonate (sat.), extracted with ethyl acetate (2×), dried with sodium sulfate, filtered, and concentrated. Purification by column chromatography (0-50% ethyl acetate/hexanes+1% TEA) provided (S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-(pyridin-2-yl)propanoate (0.558 g, 42%) as a light brown solid. MS (EI) for C20H24N2O4, found 257.2 [M-Boc]+.

来源