Реакция #1328409

Уравнение реакции

7-butyryloxy-3-benzyloxycarbonylmethylaminocarbonyl-6-chlorocoumarin

hydrogen

hydrogen

acetic acid

coumarin

coumarin

coumarin

→

7-Butyryloxy-3-carboxymethylaminocarbonyl-6-chlorocoumarin

Растворители

dioxane

Условия реакции

Обработка

1. 1
   Фильтрацияwas filtered
2. 2
   workup.ADDITIONThe product containing carbon
3. 3
   Экстракцияwas extracted five times with 25 ml
4. 4
   Температураto cool upon which the product
5. 5
   Другоеprecipitated as a white powder
6. 6
   ДругоеReduction of the solvent to 20 ml precipitates more product
7. 7
   ТемператураThe remaining dioxane solution is heated
8. 8
   workup.ADDITIONheptane is added until the solution

Методика

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 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): δ 1.02 ppm (t, 3H, J=7.4 Hz, butyric methyl), δ 1.73 ppm (m, 2H, J1≈J2=7.3 Hz, butyric methylene), δ 2.70 ppm (t, 2H, J=7.2 Hz, butyric methylene), δ 4.07 ppm (d, 2H, J=5.6 Hz, glycine methylene), δ 7.67 ppm (s, 1H, coumarin), δ 8.35 ppm (s, 1H, coumarin), δ 8.90 ppm (s, 1H, coumarin), δ 9.00 ppm (t, 1H, J=5.6 Hz, amide).

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