反応 #61105

反応方程式

2-Amino-thiazole-4-carboxylic acid methyl ester

(2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid

1-hydroxybenzotriazole

→

2-((2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyrylamino)-thiazole-4-carboxylic acid methyl ester

収率 43.0%

溶媒

N,N-dimethylformamide

ethyl acetate

反応条件

後処理

1. 1
   洗浄washed with water, brine
2. 2
   乾燥dried (magnesium sulfate)
3. 3
   その他Evaporation of the solvents and chromatography of the residue over silica gel gradient
4. 4
   洗浄eluted with 0.2-1.5% methanol in dichloromethane

実験手順

2-Amino-thiazole-4-carboxylic acid methyl ester (0.57 g, 3.62 mmol) and (2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid (Acros) (1.01 g, 3.62 mmol), 1-hydroxybenzotriazole and (0.59 g, 4.34 mmol) and O-benzeotrazol-1-yl-N,N,N′,N′-tetramethyluroniumhexaflurorophosphate (1.65 g, 4.34 mmol) in N,N-dimethylformamide (8 mL) were stirred at ambient temperature for 24 hours. The mixture was diluted with ethyl acetate, washed with water, brine and dried (magnesium sulfate). Evaporation of the solvents and chromatography of the residue over silica gel gradient eluted with 0.2-1.5% methanol in dichloromethane gave 2-((2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyrylamino)-thiazole-4-carboxylic acid methyl ester (0.65 g, 43%).

出典