反应 #2003

反应方程式

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

D-tryptophan benzyl ester

1-hydroxybenztriazole hydrate

t-butoxycarbonyl-α-methylalanine

→

(R)-α-[(2-t-Butoxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, benzyl ester

溶剂

water

chloroform

反应条件

后处理

1. 1
   其他The chloroform layer was separated
2. 2
   洗涤washed with 5% aqueous citric acid solution (25 mL) and 5% aqueous sodium bicarbonate solution (25 mL)
3. 3
   干燥The chloroform layer was dried over magnesium sulfate
4. 4
   过滤filtered
5. 5
   其他evaporated under vacuum
6. 6
   其他to afford a thick oily foam
7. 7
   其他afforded a yellow foam (0.822 g 50%)

实验过程

Crude D-tryptophan benzyl ester (1.0 g, 3.40 mmol), 1-hydroxybenztriazole hydrate (0.63 g, 4.1 mmol) and t-butoxycarbonyl-α-methylalanine (0.84 g, 4.11 mmol) were stirred together at room temperature in chloroform (20 mL). 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (980 mg, 5.11 mmol) was added to this mixture in a single portion. The reaction mixture was stirred at room temperature for 4 hours and worked up by pouring into water (50 mL). The chloroform layer was separated and washed with 5% aqueous citric acid solution (25 mL) and 5% aqueous sodium bicarbonate solution (25 mL). The chloroform layer was dried over magnesium sulfate, filtered and evaporated under vacuum to afford a thick oily foam. Chromatography on silica gel using ethyl acetate/hexanes (2:3 v/v) afforded a yellow foam (0.822 g 50%).

来源