反応 #82343

反応方程式

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

収率 42.3%

溶媒

ethyl acetate

tetrahydrofuran

反応条件

後処理

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

実験手順

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).

出典