反应 #2308000

反应方程式

N-methylmorpholine

EDC

HOBt

N-(tert-butoxycarbonyl)-3-tert-butyl-D-alanine

3-(3-pyridyl)-L-alanine methyl ester

→

N-(tert-Butoxycarbonyl)-3-(tert-butyl)-D-alanyl-3-(3-pyridyl)-L-alanine methyl ester

溶剂

dichloromethane

dichloromethane

反应条件

后处理

1. 1
   其他The reaction mixture slowly (approx. 12 h)
2. 2
   其他warms to room temperature, with complete conversion
3. 3
   洗涤washing with saturated sodium bicarbonate solution (10 ml)
4. 4
   干燥The organic phase is dried with magnesium sulphate
5. 5
   过滤filtered
6. 6
   浓缩concentrated
7. 7
   其他The crude product is purified by flash chromatography (silica gel, gradient dichloromethane 100% to dichloromethane/methanol: 4/1)
8. 8
   其他resulting in 466 mg (96% of theory) of product

实验过程

N-methylmorpholine (5 equivalents, 6.0 mmol), EDC (2.5 equivalents, 3.0 mmol) and HOBt (2.5 equivalents, 3.0 mmol) are added slowly to a solution of N-(tert-butoxycarbonyl)-3-tert-butyl-D-alanine (1.0 equivalent, 1.2 mmol) and 3-(3-pyridyl)-L-alanine methyl ester (1.0 equivalent, 1.2 mmol) in dry dichloromethane (3 ml) at −30° C. The reaction mixture slowly (approx. 12 h) warms to room temperature, with complete conversion being observed by means of HPLC (method 36). The reaction mixture is worked up by diluting with dichloromethane (20 ml) and washing with saturated sodium bicarbonate solution (10 ml). The organic phase is dried with magnesium sulphate, filtered and concentrated. The crude product is purified by flash chromatography (silica gel, gradient dichloromethane 100% to dichloromethane/methanol: 4/1), resulting in 466 mg (96% of theory) of product.

来源