반응 #7439

반응 방정식

hydrogen

7-butyryloxy-3-benzyloxycarbonylmethylaminocarbonyl-6-chlorocoumarin

acetic acid

hydrogen

→

7-Butyryloxy-3-carboxymethylaminocarbonyl-6-chlorocoumarin

용매

dioxane

반응 조건

후처리

1. 1
   여과was filtered
2. 2
   workup.ADDITIONThe product containing carbon
3. 3
   추출was extracted five times with 25 ml
4. 4
   온도to cool upon which the product
5. 5
   기타precipitated as a white powder
6. 6
   기타Reduction of the solvent to 20 ml precipitates more product
7. 7
   온도The remaining dioxane solution is heated
8. 8
   workup.ADDITIONis added until the solution

실험 절차

7-Butyryloxy-3-carboxymethylaminocarbonyl-6-chlorocoumarin was prepared as follows. 920 mg (2 mMol) 7-butyryloxy-3-benzyloxycarbonylmethylaminocarbonyl-6-chlorocoumarin were dissolved in 50 ml dioxane. 100 mg palladium on carbon (10%) and 100 microliters acetic acid were added to the solution and the suspension stirred vigorously in a hydrogen atmosphere at ambient pressure. After the uptake of hydrogen seized the suspension was filtered. The product containing carbon was extracted five times with 25 ml boiling dioxane. The combined dioxane solutions were let to cool upon which the product precipitated as a white powder. Reduction of the solvent to 20 ml precipitates more product. The remaining dioxane solution is heated to boiling and to heptane is added until the solution becomes cloudy. The weights of the dried powders were 245 mg, 389 mg and 58 mg, totaling 692 mg (1.88 mMol, 94%) of white product. 1H NMR (dDMSO): 102 ppm (t, 3H, J=7.4 Hz, butyric methyl), 1.73 ppm (m, 2H, J1 J2=7.3 Hz, butyric methylene), 2.70 ppm (t, 2H, J=7.2 Hz, butyric methylene), 4.07 ppm (d, 2H, J=5.6 Hz, glycine methylene), 7.67 ppm (s, 1H, coumarin), 8.35 ppm (s, 1H, coumarin), 8.90 ppm (s, 1H, coumarin), 9.00 ppm (t, 1H, J=5.6 Hz, amide).

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