반응 #78647

반응 방정식

N-tert-butyloxycarbonylglycine

N,N,N′,N′-tetramethyluronium tetrafluoroborate

triethylamine

3-amino-4-methylaminobenzoic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide

→

3-[(N-tert-Butoxycarbonylamino)acetylamino]-4-methylaminobenzoic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide

용매

dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for 2 hours
2. 2
   기타The grey precipitate formed
3. 3
   여과was filtered off
4. 4
   세척washed with water
5. 5
   기타dried
6. 6
   기타recrystallized from ethyl acetate with the addition of activated charcoal

실험 절차

19.2 g (0.11 mol) of N-tert-butyloxycarbonylglycine were dissolved in 175 mL of dimethylformamide, mixed with 35.2 g (0.11 mol) of O-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, 11.0 g of triethylamine, and 34.2 g (0.10 mol) of 3-amino-4-methylaminobenzoic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide and stirred for 2.5 hours at ambient temperature. Then the reaction solution was mixed with 5 l of ice water and stirred for 2 hours. The grey precipitate formed was filtered off, washed with water, dried, and recrystallized from ethyl acetate with the addition of activated charcoal. Yield: 39.85 g (80% of theory), C25H33N5O6 (499.6); Rf value: 0.55 (silica gel; methylene chloride/ethanol=19:1).

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