反应 #82343

反应方程式

dicyclohexylcarbodiimide

hydroxybenzotriazole

N-ethylmorpholine

N2 [3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1 -phenyl-L-prolinamide

N-(benzyloxycarbonyl)-L-asparagine

→

N2 [3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -phenyl-L-prolinamide

收率 42.3%

溶剂

ethyl acetate

tetrahydrofuran

反应条件

后处理

1. 1
   过滤filtered
2. 2
   洗涤The filtrate was washed with sodium bicarbonate solution and sodium chloride solution
3. 3
   其他the solvent was then removed by evaporation
4. 4
   其他The residue was chromatographed on silica gel
5. 5
   洗涤for the elution

实验过程

0.208 g of dicyclohexylcarbodiimide, 0.124 g of hydroxybenzotriazole and 0.106 g of N-ethylmorpholine were added to a stirred solution of 0.315 g of N2 -[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1 -phenyl-L-prolinamide and 0.244 g of N-(benzyloxycarbonyl)-L-asparagine in 10 ml of tetrahydrofuran at 0° C. The mixture was stirred for 16 hours, then diluted with ethyl acetate and filtered. The filtrate was washed with sodium bicarbonate solution and sodium chloride solution and the solvent was then removed by evaporation. The residue was chromatographed on silica gel using dichloromethane/methanol (9:1) for the elution to give 0.22 g of N2 -[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -phenyl-L-prolinamide in the form of a white solid of melting point 169°-171° C. (from methanol).

来源