反応 #45277

反応方程式

ethyl ether

N-(Benzyloxycarbonyl)-α-phosphonoglycine trimethyl ester

1,8-diazabicyclo[5,4,0]undec-7-ene

2,6-difluorobenzaldehyde

→

2-benzyloxycarbonylamino-3-(2,6-difluorophenyl)acrylic acid methyl ester

収率 72.0%

溶媒

methylene chloride

methylene chloride

反応条件

後処理

1. 1
   温度cooled to <−30° C
2. 2
   workup.STIRRINGThe reaction mixture was stirred for another 20 min
3. 3
   温度to warm up to room temperature for 30 min
4. 4
   洗浄washed with 1 N HCl, brine
5. 5
   乾燥dried over MgSO4
6. 6
   その他Rotary evaporation

実験手順

N-(Benzyloxycarbonyl)-α-phosphonoglycine trimethyl ester (Aldrich No. 37, 635-3; 6.7 g, 20 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (Aldrich No. 13, 900-9; 3.3 mL, 22 mmol) were dissolved in methylene chloride (11 mL) and stirred at room temperature for 15 min, and then cooled to <−30° C. A solution of 2,6-difluorobenzaldehyde (1.9 mL, 20 mmol) in methylene chloride (25 mL) was added to the reaction mixture dropwise over 20 min. The reaction mixture was stirred for another 20 min, and then allowed to warm up to room temperature for 30 min. The reaction mixture was then poured into ethyl ether (300 mL) and washed with 1 N HCl, brine and dried over MgSO4. Rotary evaporation gave crude 2-benzyloxycarbonylamino-3-(2,6-difluorophenyl)acrylic acid methyl ester which was purified by chromatography on a Medium Pressure Liquid Column (MPLC) eluting with 20% ethyl acetate/80% hexane to give pure product (5 g, 72% yield, liquid).

出典