반응 #42343

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N-methylpropylamine

3-iodo-5-(methoxycarbonyl)benzoic acid

diisopropylethylamine

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

→

title compound

Methyl 3-iodo-5-{[methyl(propyl)amino]carbonyl}benzoate

용매

ethyl acetate

DMF

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후처리

1. 1
   세척washed with water, saturated sodium bicarbonate, and brine
2. 2
   건조The organic layer is dried over sodium sulfate
3. 3
   여과filtered
4. 4
   농축concentrated under reduced pressure

실험 절차

To 3-iodo-5-(methoxycarbonyl)benzoic acid (1.0 g, 3.3 mmol), prepared as in Example SP-281, step 1, and diisopropylethylamine (1.7 mL, 9.8 mmol) in DMF (10 mL) is added O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 1.5 g, 3.9 mmol) then N-methylpropylamine (503 μL, 4.9 mmol). The solution is stirred at room temperature 2 h. The solution is diluted in ethyl acetate and washed with water, saturated sodium bicarbonate, and brine. The organic layer is dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound in crude form. This material is purified by flash chromatography (40% ethyl acetate/hexane) to give the purified title compound. MS (ESI) [M+H+]=362.4.

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